European Journal of Organic Chemistry
10.1002/ejoc.201901607
FULL PAPER
1
needles in 90% yield (35 mg). H NMR (600 MHz, CDCl
8
8
3
): δ 7.73 (d, J =
127.1, 126.0, 42.6, 32.7, 31.1, 21.5 ppm. Spectral data are in agreement
with literature data.[34] MS (APCI, m/z): calcd for C16
H
20NO
+
.3 Hz, 2H), 7.52 (d, J = 8.1 Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H), 7.29 (d, J =
.0 Hz, 2H), 4.78 (t, J = 6.2 Hz, 1H), 4.21 (d, J = 6.4 Hz, 2H), 2.43 (s, 3H)
): δ 143.7, 140.4, 136.7, 130.4, 130.2,
2
S [M-H] : 290.1,
found: 290.1.
ppm. 13C NMR (151 MHz, CDCl
3
1
4
29.9, 129.8, 129.7, 128.0, 127.1, 126.6, 125.5, 125.5, 124.8, 123.0, 121.2,
4
-Methyl-N-propylbenzenesulfonamide (5b): This compound was
6.7, 21.5 ppm. Spectral data are in agreement with literature data.[ MS
23]
prepared from 0.11 mmol of imine 4b to give 5b as yellow liquid in
quantitative yield (23 mg). H NMR (600 MHz, CDCl
-
(APCI, m/z): calcd for C15
H
13
F
3
NO
2
S [M-H] : 328.0, found: 328.0.
1
3
): δ 7.75 (d, J = 8.0
Hz, 2H), 7.31 (d, J = 7.9 Hz, 2H), 4.62 (t, J = 5.6 Hz, 1H), 2.90 (dd, J =
13.6, 6.8 Hz, 2H), 2.43 (s, 3H), 1.55 – 1.41 (m, 2H), 0.86 (t, J = 7.4 Hz, 3H)
4
-Methyl-N-[(4-nitrophenyl)methyl]-benzenesulfonamide (3t): This
compound was prepared from 0.11 mmol of imine 2t to give 3t as yellow
solid in 65% yield (22 mg). H NMR (600 MHz, CDCl
Hz, 2H), 7.75 (d, J = 8.3 Hz, 2H), 7.42 (d, J = 8.7 Hz, 2H), 7.32 (d, J = 8.0
Hz, 2H), 4.85 (t, J = 6.3 Hz, 1H), 4.26 (d, J = 6.5 Hz, 2H), 2.44 (s, 3H) ppm.
13C NMR (151 MHz, CDCl
ppm. 13C NMR (151 MHz, CDCl
3
): δ 143.3, 137.0, 129.7, 127.1, 44.9, 22.9,
1
[35]
3
): δ 8.14 (d, J = 8.7
21.5, 11.1 ppm. Spectral data are consistent with those in the literature.
+
MS (APCI, m/z): calcd for C10
H
16NO
2
S [M+H] : 214.1, found: 214.1.
3
): δ 144.4, 143.8, 136.7, 129.9, 128.4, 127.1,
N-(3-Methylbutyl)-4-methylbenzenesulfonamide (5c): This compound
126.4, 46.4, 21.5 ppm. Spectral data are consistent with those in the
was prepared from 0.11 mmol of imine 4c to give 5c as yellow liquid in
[
32]
-
literature. MS (APCI, m/z): calcd for C14
H
13
N
2 4
O
S [M-H] : 305.1, found:
1
quantitative yield (27 mg). H NMR (600 MHz, CDCl
3
): δ 7.76 (d, J = 7.9
3
05.2.
Hz, 2H), 7.31 (d, J = 7.8 Hz, 2H), 4.61 (bs, 1H), 2.94 (dd, J = 13.8, 6.8 Hz,
H), 2.43 (s, 2H), 1.58 (tt, J = 13.2, 6.6 Hz, 1H), 1.34 (dd, J = 14.3, 7.1 Hz,
1H), 0.82 (d, J = 6.6 Hz, 6H) ppm. 13C NMR (151 MHz, CDCl
): δ 143.3,
2
4-Methyl-N-(naphthalen-2-ylmethyl)benzenesulfonamide (3u): This
3
compound was prepared from 0.11 mmol of imine 2u to give 3u as white
136.9, 129.6, 127.1, 41.5, 38.3, 25.4, 22.2, 21.5 ppm. Spectral data are
1
[36]
solid in quantitative yield (34 mg). H NMR (600 MHz, CDCl
3
): δ 7.78 (dd,
consistent with those in the literature.
MS (APCI, m/z): calcd for
+
J = 6.0, 3.4 Hz, 1H), 7.77 – 7.73 (m, 3H), 7.71 (dd, J = 6.0, 3.4 Hz, 1H),
C
12
H
2
20NO S [M+H] : 241.1, found: 242.1.
7
7
2
1
4
.59 (s, 1H), 7.46 (dd, J = 6.2, 3.2 Hz, 2H), 7.30 (dd, J = 8.4, 1.4 Hz, 1H),
.25 (d, J = 8.4 Hz, 2H), 4.95 (t, J = 5.8 Hz, 1H), 4.27 (d, J = 6.3 Hz, 2H),
.39 (s, 3H) ppm. 13C NMR (151 MHz, CDCl
): δ 143.5, 136.9, 133.6, 133.2,
3
3
-Methyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide (7a): This
compound was prepared from 0.12 mmol of imine 6a to give 7a as
colorless solid in quantitative yield (22 mg). H NMR (600 MHz, CDCl
32.8, 129.7, 128.5, 127.73, 127.68, 127.2, 126.7, 126.3, 126.1, 125.7,
1
3
): δ
7.4, 21.5 ppm. Spectral data are consistent with those in the literature.[
33]
7.77 (d, J = 7.8 Hz, 1H), 7.63 (dd, J = 11.2, 3.9 Hz, 1H), 7.52 (t, J = 7.6 Hz,
1H), 7.39 (d, J = 7.8 Hz, 1H), 4.90 (s, 1H), 4.83 – 4.75 (m, 1H), 1.62 (d, J
6.7 Hz, 3H) ppm. 13C NMR (151 MHz, CDCl
= ): δ 141.7, 135.5, 133.2,
-
MS (APCI, m/z): calcd for C18
H
16NO
2
S [M-H] : 310.1, found: 310.2.
3
N-(4-Chlorobenzyl)-5-methylpyridine-2-sulfonamide
(3v):
This
129.2, 123.9, 121.2, 53.4, 21.4 ppm. Spectral data are in agreement with
literature data.[37] MS (APCI, m/z): calcd for C
-
compound was prepared from 0.068 mmol of imine 2v to give 3v as
8
H
8 2
NO S [M-H] : 182.0,
1
colorless crystals in 91% yield (32 mg). H NMR (600 MHz, CDCl
3
): δ 8.34
found: 182.0.
(
7
d, J = 1.2 Hz, 1H), 7.83 (d, J = 7.9 Hz, 1H), 7.64 (dd, J = 7.9, 1.3 Hz, 1H),
.19 (s, 4H), 6.32 (t, J = 6.0 Hz, 1H), 4.17 (d, J = 6.4 Hz, 2H) ppm. 13C
): δ 154.5, 150.3, 138.1, 137.3, 135.1, 133.5, 129.5,
28.6, 128.6, 122.1, 46.8, 18.5 ppm. HRMS (ESI+, m/z): calcd for
1
-Phenyl-N-tosylethanamine (7b): This compound was prepared from
NMR (151 MHz, CDCl
1
C
3
1
0
.11 mmol of imine 6b to give 7b as white solid in 93% yield (28 mg). H
): δ 7.62 (d, J = 8.2 Hz, 2H), 7.18 (t, J = 7.7 Hz, 5H),
.10 (d, J = 7.7 Hz, 2H), 4.95 (d, J = 6.8 Hz, 1H), 4.46 (p, J = 6.9 Hz, 1H),
.38 (s, 3H), 1.42 (d, J = 6.9 Hz, 3H) ppm. 13C NMR (151 MHz, CDCl
): δ
NMR (600 MHz, CDCl
3
+
13 2 2
H13ClN O SK [M+K] : 335.00178, found: 335.00193.
7
2
3
N-(4-Chlorobenzyl)thiophene-2-sulfonamide (3x): This compound was
143.1, 142.0, 137.6, 129.4, 128.5, 127.4, 127.1, 126.1, 53.6, 23.5, 21.5
ppm. Spectral data are in agreement with literature data.[ MS (APCI,
38]
prepared from 0.068 mmol of imine 2x to give 3x as colorless solid in 96%
1
-
yield (15 mg). H NMR (600 MHz, CDCl
3
): δ 7.63 – 7.58 (m, 2H), 7.27 (dd,
m/z): calcd for C15
H
16NO
2
S [M-H] : 274.1, found: 274.1.
J = 6.9, 1.5 Hz, 2H), 7.17 (d, J = 8.4 Hz, 2H), 7.09 (dt, J = 8.2, 4.1 Hz, 1H),
.94 (t, J = 5.8 Hz, 1H), 4.19 (d, J = 6.3 Hz, 2H) ppm. 13C NMR (151 MHz,
4
N-(1-Phenylethyl)methanesulfonamide (7c): This compound was
CDCl
3
): δ 135.9, 129.7, 129.1, 127.7, 127.4, 124.5, 124.1, 124.1, 122.7,
prepared from 0.11 mmol of imine 6c to give 7c as colorless oil in
+
42.0 ppm. HRMS (ESI+, m/z): calcd for C11
H
10ClNO
2 2
S K [M+K] : 327.9444,
1
quantitative yield (22 mg). H NMR (600 MHz, CDCl
3
): δ 7.40 – 7.33 (m,4H),
found: 327.9441.
7
(
.32 – 7.28 (m, 1H), 4.98 (d, J = 6.5 Hz, 1H), 4.65 (p, J = 6.9 Hz, 1H), 2.61
s, 3H), 1.54 (d, J = 6.9 Hz, 3H) ppm. 13C NMR (151 MHz, CDCl
3
): δ 142.6,
N-(4-Chlorobenzyl)-3-methylpyridin-2-amine (3y): This compound was
prepared from 0.11 mmol of imine 2y to give 3y as white solid in
129.2, 128.2, 126.4, 54.0, 42.0, 24.2 ppm. Spectral data are in agreement
with literature data.[39] MS (APCI, m/z): calcd for C
found: 198.1.
12NO
-
9
H
2
S [M-H] : 198.1,
quantitative yield (25 mg). 1H NMR (600 MHz, CDCl
): δ 8.05 – 8.01 (m,
H), 7.34 – 7.27 (m, 4H), 7.25 (dd, J = 7.1, 0.8 Hz, 1H), 6.56 (dd, J = 7.1,
.1 Hz, 1H), 4.67 (d, J = 5.5 Hz, 2H), 4.37 (s, 1H), 2.10 (s, 3H) ppm. 13C
): δ 156.4, 145.5, 138.7, 136.9, 132.8, 129.1, 116.5,
3
1
5
NMR tests of functional group tolerance
NMR (151 MHz, CDCl
3
1
13.1, 45.0, 17.0 ppm. HRMS (ESI+, m/z): calcd for C13
H
14ClN
2
[M+H]+:
Imine 2a (20 mg, 0.077 mmol, 1.0 equiv), additive (0.077 mmol, 1.0 equiv)
and Schwarz reagent (20 mg, 0.077 mmol, 1.0 equiv) were added to a
flame-dried flask and dissolved in anhydrous DCM (0.4 mL) and stirred at
r.t. for 20 min. After this time, DCM (3 mL) and benzoyl benzoate (14µL,
233.0840, found: 233.08400.
N-(3-Phenylpropyl)-4-methylbenzenesulfonamide
(5a):
This
compound was prepared from 0.11 mmol of imine 4a to give 5a as yellow
0
.077 mmol, 1.0 equiv) were added and the solvent was evaporated. The
1
liquid in quantitative yield (32 mg). H NMR (600 MHz, CDCl
3
): δ 7.74 (d, J
crude mixture was dissolved in CDCl
remove most of the Schwartz residue, and H NMR was measured.
3
, filtered through a syringe filter to
=
7
8.2 Hz, 2H), 7.29 (d, J = 8.0 Hz, 2H), 7.24 (t, J = 8.0 Hz, 2H), 7.17 (t, J =
.4 Hz, 1H), 7.07 (d, J = 7.3 2Hz, 1H), 4.72 (t, J = 6.0 Hz, 1H), 2.95 (q, J =
.7 Hz, 2H), 2.63 – 2.55 (m, 2H), 2.42 (s, 3H), 1.83 – 1.72 (m, 2H) ppm.
1
6
.
1
3C NMR (151 MHz, CDCl
3
): δ 143.4, 140.9, 136.9, 129.7, 128.4, 128.3,
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