LOBANOVA et al.
1292
N-[2-(1-Ethoxyethoxy)ethyl]-2,2,2-trifluoroacet-
N-[3-(1-Butoxyethoxy)propyl]-2,2,2-trifluoro-
acetamide (IIId). Yield 6.61 g (81%), bp 100–102°C
(1 mm), nD20 = 1.4100. IR spectrum, ν, cm–1: 3533,
3319, 3102, 2989, 2961, 2937, 2876, 1726, 1711,
1557, 1467, 1456, 1436, 1381, 1342, 1250, 1209,
1182, 1163, 1138, 1098, 1073, 1032, 994, 979, 951,
amide (IIIa). Yield 3.52 g (51%), bp 101–103°C
(5 mm), nD20 = 1.4008. IR spectrum, ν, cm–1: 3522,
3442, 3314, 3101, 2984, 2939, 2886, 1713, 1557,
1471, 1446, 1383, 1343, 1279, 1212, 1184, 1160, 1138,
1086, 1059, 956, 870, 846, 772, 725, 665, 522, 421.
1H NMR spectrum (CDCl3), δ, ppm: 1.19 t (3H,
1
914, 841, 773, 753, 724, 666, 520. H NMR spectrum
3
3
3
MeCH2O, J = 7.1 Hz), 1.29 d (3H, MeCH, J =
(CDCl3), δ, ppm: 0.91 t (3H, MeCH2, J = 7.3 Hz),
3
5.3 Hz), 3.44–3.71 m (6H, OCH2, CH2N), 4.68 q (1H,
1.29 d (3H, MeCH, J = 5.3 Hz), 1.38 m (2H,
3
CH, J = 5.3 Hz), 7.41 br.s (1H, NH). 13C NMR spec-
MeCH2), 1.54 m (2H, MeCH2CH2), 1.85 m (2H,
CH2CH2N), 3.37–3.79 m (6H, OCH2, CH2N), 4.65 q
trum (CDCl3), δC, ppm: 16.3 (MeCH2O), 20.8 (MeCH),
41.3 (CH2N), 62.7 (MeCH2O), 64.1 (OCH2CH2N),
101.3 (CH), 117.2 (CF3, J = 288.4 Hz), 158.6 (C=O,
2J = 36.8 Hz). Found, %: C 41.98; H 6.47; F 24.22;
N 6.14. C8H14F3NO3. Calculated, %: C 41.92; H 6.16;
F 24.87; N 6.11.
3
(1H, CH, J = 5.3 Hz), 7.70 br.s (1H, NH). 13C NMR
spectrum (CDCl3), δC, ppm: 13.7 (MeCH2), 19.3
(MeCH2), 19.6 (MeCH), 28.2 (CH2CH2N), 31.9
(MeCH2CH2), 39.0 (CH2N), 64.7 (MeCH2CH2CH2O),
65.5 (OCH2CH2CH2N), 100.2 (CH), 116.0 (CF3, J =
2
287.4 Hz), 157.0 (C=O, J = 36.8 Hz). Found, %:
N-[2-(1-Butoxyethoxy)ethyl]-2,2,2-trifluoroacet-
amide (IIIb). Yield 6.76 g (88%), bp 137–138°C
(13 mm), nD20 = 1.4069. IR spectrum, ν, cm–1: 3518,
3441, 3313, 3101, 2990, 2962, 2938, 2877, 1727,
1712, 1557, 1459, 1435, 1382, 1344, 1212, 1183,
1163, 1138, 1095, 1074, 978, 956, 942, 905, 875, 772,
C 48.24; H 7.34; F 21.65; N 5.31. C11H20F3NO3. Cal-
culated, %: C 48.70; H 7.43; F 21.01; N 5.16.
N-[1-(1-Ethoxyethoxy)-2-methylpropan-2-yl]-
2,2,2-trifluoroacetamide (IIIe). Yield 4.66 g (60%),
bp 103–105°C (13 mm), nD20 = 1.4022. IR spectrum, ν,
cm–1: 3445, 3407, 3313, 3094, 2983, 2939, 2905, 2883,
1722, 1717, 1557, 1538, 1477, 1461, 1386, 1369,
1342, 1299, 1282, 1212, 1184, 1157, 1112, 1088, 1059,
999, 946, 933, 915, 882, 844, 817, 789, 773, 726, 628,
1
725, 667, 637, 627, 521, 422. H NMR spectrum
3
(CDCl3), δ, ppm: 0.91 t (3H, MeCH2, J = 7.3 Hz),
3
1.30 d (3H, MeCH, J = 5.3 Hz), 1.36 m (2H,
MeCH2), 1.54 m (2H, MeCH2CH2), 3.37–3.70 m (6H,
3
1
OCH2, CH2N), 4.67 q (1H, CH, J = 5.3 Hz), 6.95 br.s
586, 573, 545, 524, 466. H NMR spectrum (CDCl3),
(1H, NH). 13C NMR spectrum (CDCl3), δC, ppm: 13.6
(MeCH2), 19.2 (MeCH2), 19.4 (MeCH), 31.7
(MeCH2CH2), 39.9 (CH2N), 62.9 (MeCH2CH2CH2O),
65.9 (OCH2CH2N), 100.2 (CH), 115.8 (CF3, J =
δ, ppm: 1.06 t (3H, MeCH2O, 3J = 7.1 Hz), 1.16 d (3H,
3
MeCH, J = 5.3 Hz), 1.23–1.27 m (6H, Me2C), 3.29–
3
3.51 m (4H, OCH2), 4.53 q (1H, CH, J = 5.3 Hz),
6.90 br.s (1H, NH). 13C NMR spectrum (CDCl3), δC,
ppm: 14.8 (MeCH2O), 19.4 (MeCH), 22.6 and 22.7
(Me2C), 54.6 (Me2C), 61.7 (MeCH2O), 71.5
(OCH2CMe2), 100.2 (CH), 115.5 (CF3, J = 289.0 Hz),
2
287.5 Hz), 157.2 (C=O, J = 37.1 Hz). Found, %:
C 46.47; H 7.34; F 22.94; N 5.14. C10H18F3NO3. Cal-
culated, %: C 46.69; H 7.05; F 22.16; N 5.44.
2
156.3 (C=O, J = 36.3 Hz). Found, %: C 46.34;
N-[3-(1-Ethoxyethoxy)propyl]-2,2,2-trifluoro-
acetamide (IIIc). Yield 4.09 g (56%), bp 110–112°C
(3 mm), nD20 = 1.4025. IR spectrum, ν, cm–1: 3511,
3317, 3102, 2982, 2937, 2884, 1727, 1711, 1556,
1476, 1447, 1382, 1342, 1208, 1183, 1162, 1137, 1099,
1084, 1059, 994, 955, 929, 879, 845, 785, 773, 724,
H 7.08; F 22.99; N 5.85. C10H18F3NO3. Calculated, %:
C 46.69; H 7.05; F 22.16; N 5.44.
N-[1-(1-Butoxyethoxy)-2-methylpropan-2-yl]-
2,2,2-trifluoroacetamide (IIIf). Yield 4.21 g (49%),
bp 103–105°C (4 mm), nD20 = 1.4068. IR spectrum, ν,
cm–1: 3444, 3411, 3319, 3092, 2986, 2963, 2938, 2877,
1724, 1680, 1554, 1535, 1476, 1461, 1403, 1386,
1368, 1344, 1298, 1283, 1246, 1211, 1182, 1158, 1135,
1096, 1074, 1055, 1034, 1001, 978, 953, 916, 885,
839, 801, 789, 773, 726, 627, 523, 468. 1H NMR spec-
1
668, 562, 522, 420. H NMR spectrum (CDCl3), δ,
3
ppm: 1.19 t (3H, MeCH2O, J = 6.9 Hz), 1.29 d (3H,
3
MeCH, J = 5.0 Hz), 1.86 m (2H, CH2CH2N), 3.44–
3
3.75 m (6H, OCH2, CH2N), 4.66 q (1H, CH, J =
5.0 Hz), 7.76 br.s (1H, NH). 13C NMR spectrum
(CDCl3), δC, ppm: 14.9 (MeCH2O), 19.5 (MeCH),
28.0 (CH2CH2N), 38.7 (CH2N), 61.0 (MeCH2O), 64.3
(OCH2CH2CH2N), 99.9 (CH), 115.9 (CF3, J =
3
trum (CDCl3), δ, ppm: 0.91 t (3H, MeCH2, J =
7.4 Hz), 1.29 d (3H, MeCH, 3J = 5.3 Hz), 1.32–1.41 m
(8H, Me2C, MeCH2), 1.54 m (2H, MeCH2CH2), 3.37–
2
3
287.7 Hz), 157.0 (C=O, J = 36.8 Hz). Found, %:
3.60 m (4H, OCH2), 4.65 q (1H, CH, J = 5.3 Hz),
C 44.96; H 6.59; F 23.37; N 5.48. C9H16F3NO3. Cal-
culated, %: C 44.44; H 6.63; F 23.43; N 5.76.
6.86 br.s (1H, NH). 13C NMR spectrum (CDCl3), δC,
ppm: 13.7 (MeCH2), 19.3 (MeCH2), 19.5 (MeCH),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 10 2012