RSC Advances
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N-Mesityl-N0-{2-[3-o-(mesitylaminooxalylaminophenoxy)pro-
poxy]-phenyl}oxamide 3d. Colorless crystals; yield 0.38 g (60%,
Method A), 0.27 g (42%, Method B), 0.22 g (35%, Method C); mp
220 ꢀC; nmax(KBr)/cmꢁ1 3357, 3290, 2953, 2922, 2885, 2859,
1677, 1600, 1539, 1510, 1485, 1453, 1330, 1289, 1254, 1113,
1043, 789, 748, 731, 712; dH(400 MHz, CDCl3) 2.21 (s, 12H), 2.30
(s, 6H), 2.39 (quint, 2H, J 6.0), 4.32 (t, 4H, J 6.0), 6.94 (s, 4H),
6.96–7.09 (m, 6H), 8.36 (d, 2H, J 8.0), 8.78 (s, 2H, NH), 10.00 (s,
2H, NH); dC(CDCl3, 100 MHz) 18.5, 21.1, 29.4, 64.7, 111.7, 119.7,
121.4, 125.5, 126.3, 129.3, 129.9, 135.0, 137.9, 148.1, 157.3,
158.7; m/z (EI) 636 (M+); m/z (EI) 636.2942 (M+, C37H40N4O6
requires 636.2942).
liquor from crystallization of 2a was subjected to column
chromatography using silica gel and elution with petroleum
ether (40–60) and ethyl acetate to give compound 9.
Bis-ethane-1,2-diamine 2a. Colorless crystals; yield 0.38 g
(78%); mp 83–85 ꢀC; nmax(KBr)/cmꢁ1 3049, 3021, 2951, 2925,
2876, 2854, 1601, 1509, 1468, 1442, 1323, 1255, 1211, 1135,
1054, 741, 693; dH(400 MHz, CDCl3) 2.26 (quint, 2H, J 6.0), 3.38
(s, 8H), 4.16 (t, 4H, J 6.0), 4.19 (br, 4H, NH), 6.60 (dd, 4H, J 8.0,
0.8), 6.67–6.74 (m, 6H), 6.79 (d, 2H, J 7.6), 6.90 (dt, 2H, J 1.6, 8.0),
7.17 (t, 4H, J 8.0); dC(CDCl3, 100 MHz) 29.4, 43.3, 43.4, 63.4,
110.6, 111.1, 113.2, 117.3, 117.8, 121.8, 129.4, 138.2, 146.3,
148.1; m/z (EI) 496 (M+); m/z (EI) 496.2832 (M+, C31H36N4O2
requires 496.2833).
N-Phenyl-N0-[o-(o-phenylaminooxalylaminophenoxymethyl)-
benzyloxyphenyl]-oxamide 3e. Buff powder; yield 0.43 g (70%);
Bis-ethane-1,2-diamine 2b. Colorless crystals; yield 0.4 g
(72%); mp 132–133 C; nmax(KBr)/cmꢁ1 3372, 3350, 3046, 3021,
mp 274–275 C; nmax(KBr)/cmꢁ1 3362, 3063, 3034, 2920, 1687,
ꢀ
ꢀ
2947, 2937, 2876, 2882, 1601, 1508, 1468, 1442, 1323, 1258,
1211, 1133, 1054, 736, 690; dH(400 MHz, CDCl3) 2.32 (quint, 2H,
J 5.6), 3.36 (m, 8H), 3.74 (s, 6H), 4.18 (t, 4H, J 5.6), 4.67 (br, 4H,
NH), 6.65 (dt, 2H, J 1.2, 7.6), 6.68 (d, 4H, J 8.8), 6.75–6.80 (m,
8H), 6.88 (dt, 2H, J 1.2, 7.6); dC(CDCl3, 100 MHz) 29.4, 43.2, 44.7,
56.0, 65.4, 110.5, 111.2, 115.05, 115.08, 117.1, 121.8, 138.3,
141.7, 146.3, 152.8; m/z (EI) 556 (M+); m/z (EI) 556.3044 (M+,
1600, 1526, 1481, 1445, 1383, 1330, 1295, 1251, 1204, 1113,
1041, 1013, 751, 710, 692; dH(400 MHz, DMSO-d6) 5.47 (s, 4H),
7.01 (t, 2H, J 7.6), 7.10 (dt, 2H, J 8.0, 1.2), 7.16 (t, 2H, J 7.6), 7.28
(d, 2H, J 8.0), 7.37 (t, 4H, J 8.0), 7.44–7.46 (m, 2H), 7.66–7.68 (m,
2H), 7.83 (t, 4H, J 8.0), 8.18 (dd, 2H, J 8.0, 1.6), 10.01 (s, 2H),
10.92 (s, 2H); dC(DMSO-d6, 100 MHz) 67.8, 112.7, 119.8, 120.7,
121.0, 124.8, 125.3, 126.0, 128.4, 128.66, 128.7, 134.7, 137.4,
147.9, 157.3, 158.2; m/z (EI) 614 (M+); m/z (EI) 614.2160 (M+,
C
33H40N4O4 requires 556.3050).
Bis-ethane-1,2-diamine 2c. Colorless crystals; yield 0.13 g
C
36H30N4O6 requires 614.2160).
(25%); mp 101–102 C; nmax(KBr)/cmꢁ1 3399, 3034, 2919, 2875,
1601, 1516, 1469, 1444, 1254, 1218, 1131, 1051, 908, 809, 772,
738; dH(400 MHz, CDCl3) 2.25 (s, 6H), 2.33 (t, 2H, J 6.0), 3.37–
3.42 (m, 8H), 4.17 (t, 4H, J 6.0), 4.17 (br, 4H, NH), 6.63–6.71 (m,
8H), 6.79 (d, 2H, J 1.2, 6.8), 6.87 (dt, 2H, J 1.2, 7.6), 7.00 (d, 4H, J
8.4); dC(100 MHz, DMSO-d6) 20.7, 29.5, 42.7, 45.6, 66.0, 110.7,
111.5, 115.5, 117.5, 121.8, 129.6, 130.0, 130.2, 138.0, 146.6; m/z
(EI) 524 (M+); m/z (EI) 524.3146 (M+, C33H40N4O2 requires
524.3146).
ꢀ
N-p-Methoxyphenyl-N0-{o-[o-(p-methoxyphenylamino)oxalyl-
aminophenoxymethyl]-benzyloxyphenyl}-oxamide 3f. Buff
precipitate; yield 0.44 g (65%); mp 220–221 C; nmax(KBr)/cmꢁ1
ꢀ
3358, 3295, 2932, 2835, 1684, 1599, 1525, 1481, 1454, 1415,
1249, 1205, 1159, 1111, 1033, 827, 750; dH(400 MHz, CDCl3) 3.81
(s, 6H), 5.35 (s, 4H), 6.90–7.00 (m, 6H), 7.03–7.07 (m, 4H), 7.42–
7.44 (m, 2H), 7.56–7.61 (m, 6H), 8.35 (dd, 2H, J 6.0, 1.2), 9.19 (s,
2H), 9.93 (s, 2H); dC(CDCl3, 100 MHz) 55.7, 69.1, 112.2, 114.5,
120.1, 121.47, 121.54, 121.7, 125.6, 126.4, 129.2, 129.4, 129.7,
134.5, 147.9, 157.2, 157.6; m/z (EI) 674 (M+); m/z (EI) 674.2371
(M+, C38H34N4O8 requires 674.2371).
N-Mesityl-N0-[o-(o-mesitylaminooxalylaminophenoxymethyl)-
benzyloxypheꢀnyl]-oxamide 3g. Buff crystals; yield 0.38 g (55%);
mp 150–151 C; nmax(KBr)/cmꢁ1 3358, 3295, 2952, 2920, 2861,
1685, 1647, 1600, 1509, 1479, 1452, 1380, 1253, 1202, 1113,
1011, 851, 750; dH(400 MHz, DMSO-d6) 2.19 (s, 12H), 2.29 (s,
6H), 5.31 (s, 4H), 6.92 (s, 4H), 6.98–7.05 (m, 6H), 7.34–7.39 (m,
2H), 7.48–7.51 (m, 2H), 8.39 (d, 2H, J 8.4), 8.76 (s, 2H), 9.93 (s,
2H); dC(CDCl3, 100 MHz) 18.5, 21.1, 69.1, 112.1, 119.9, 121.7,
125.6, 126.4, 129.0, 129.2, 129.3, 129.8, 134.3, 134.9, 137.8,
147.9, 157.4, 158.4; m/z (EI) 698 (M+); m/z (EI) 698.3099 (M+,
N,N0-Diphenylethane-1,2-diamine 9a. Colorless solid; yield
0.05 g (10%); mp 63–65 ꢀC (lit.16 mp 63–65 ꢀC); dH(400 MHz,
CDCl3) 3.41 (s, 4H), 3.80 (br, 2H, NH), 6.68 (d, 4H, J 8.4), 6.76 (t,
2H, J 7.6), 7.22 (d, 4H, J 8.0); dC(CDCl3, 100 MHz) 43.4, 113.2,
118.0, 129.5, 148.2; m/z (EI) 212 (M+).
N-Mesityl-2-o-{3-[o-(mesitylcarbamoylmethylamino)phenoxy]-
propoxy}phenylamino-acetamide 10d. Colorless crystals; yield
(0.45 g, 75%); mp 213–214 ꢀC; nmax(KBr)/cmꢁ1 3270, 3064, 3035,
2954, 2920, 2879, 1650, 1602, 1513, 1485, 1463, 1450, 1446, 1260,
1218, 1129, 1063, 1054, 854, 734; dH(400 MHz, CDCl3) 2.11 (s,
12H), 2.24 (s, 6H), 2.42 (quint, 2H, J 6.0), 3.96 (s, 4H), 4.28 (t, 4H, J
6.0), 4.99 (br, 2H, NH), 6.70 (dd, 2H, J 7.6, 1.2), 6.78 (dt, 2H, J 8.0,
1.2), 6.85 (s, 4H), 6.86 (m, 2H), 6.92 (dt, 2H, J 8.0, 1.2), 8.00 (s, 2H,
NH); dC(CDCl3, 100 MHz) 18.6, 21.1, 29.6, 49.1, 65.2, 110.9, 111.4,
119.0, 121.9, 129.1, 130.7, 135.2, 137.1, 137.2, 146.2, 169.4; m/z
(EI) 608 (M+); m/z (EI) 608.3357 (M+, C37H44N4O4 requires
C
42H42N4O6 requires 698.3098).
Synthesis of diamine 2: general procedure
A solution of lithium aluminum hydride (0.5 g, 14 mmol) in dry 608.3357).
diethyl ether (20 mL) was stirred for 5 min. Compound 3a–d
(0.9 mmol) was added and the solution was reuxed for 4–24 h.
Synthesis of bis-imidazolinium salts 1a,b
Aer cooling to room temperature, the reaction mixture was
quenched with water (0.5 mL), 15% aqueous NaOH (0.5 mL) and
Method A. HCl gas is passed for 20 min to diethylether and
the ethereal solution was collected. Aer removal of the solvent this solution was added to the above compound 2a (0.1 mmol)
in vacuo, the remaining mixture was crystallized from ethanol to in ether. A solid forms and to this solid, triethylorthoformate
give the corresponding amine derivatives 2a–c, 10. The mother (4 mL) was added and heated at 110 ꢀC for 24 h. The
38874 | RSC Adv., 2014, 4, 38869–38876
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