600
Jun Wan et al
Eluent acetone/ethanol, Yield 45%, white solid, 2.2s 4-Chloro-benzoic
acid
1-benzotriazol-1-
m.p.: 176⋅0 – 178⋅0°С; Anal. Calcd. (%): C, 59⋅50; ylmethyl-2-(2-methyl-phenyl)-2-oxo-ethyl ester (22):
H, 3⋅91; N, 9⋅05; Found(%): C, 59⋅73; H, 3⋅82; N, ethanol, Yield 48%, white solid, m.p.: 129⋅5 –
–1
8⋅97; IR, νmax/cm (KBr): 1723, 1695 (s, C=O),
131⋅5°С; Anal. Calcd. (%): C, 65⋅79; H, 4⋅32; N,
1
1575 (C=N), 1247, 1106 (s, C–O); H NMR (CDCl3): 10⋅01; Found: C, 65⋅51; H, 4⋅11; N, 9⋅82; IR,
2⋅39 (3H, methyl, CH3), 5⋅46, 5⋅55 ( J = 14⋅95; 2H,
CH2), 6⋅76 ( J = 8⋅5; 1H, CH), 7⋅28–7⋅99 (12H, 1228, 1106 (s, C–O); H NMR (CDCl3): 2⋅60 (3H,
HAr).
2
–1
max/cm (KBr): 1724, 1693 (s, C=O), 1586 (C=N),
ν
3
1
2
CH3), 5⋅42, 5⋅71 ( J = 14⋅75; d, 2H, CH2), 6⋅32
3
( J = 8⋅5; 1H, CH), 7⋅49–8⋅17 (12H, HAr).
2.2o 2-Methyl-benzoic acid 1-benzotriazol-1-
ylmethyl-2-(4-bromo-phenyl)-2-oxo-ethyl ester (18):
acetone/ethanol, Yield 44%, white solid, m.p.:
179⋅5 – 181⋅0°С; Anal. Calcd. (%): C, 59⋅50; H,
3⋅91; N, 9⋅05; Found (%): C, 59⋅37; H, 3⋅84; N,
2.2t 2-Chloro-benzoic
acid
1-benzotriazol-1-
ylmethyl-2-(2-methyl-phenyl)-2-oxo-ethyl ester (23):
ethanol, Yield 47%, white solid, m.p.: 118⋅5 –
120⋅0°С; Anal. Calcd. (%): C, 65⋅79; H, 4⋅32; N,
–1
8⋅87; IR, νmax/cm (KBr): 1719, 1688 (s, C=O),
10⋅01; Found: C, 66⋅04; H, 4⋅16; N, 9⋅84; IR,
ν
1
–1
max/cm (KBr): 1726, 1696 (s, C=O), 1588 (C=N),
1587 (C=N), 1253, 1077 (s, C–O); H NMR
1
(CDCl3): 2⋅39 (3H, methyl, CH3), 5⋅47, 5⋅55
1227, 1107 (s, C–O); H NMR (CDCl3): 2⋅40 (3H,
2
3
2
( J = 14⋅85; 2H, CH2), 6⋅77 ( J = 8⋅3; 1H, CH),
7⋅28–7⋅81 (12H, HAr).
CH3), 5⋅39, 5⋅41 ( J = 14⋅95; d, 2H, CH2), 6⋅73
3
( J = 8⋅3; 1H, CH), 7⋅30–7⋅58 (12H, HAr).
2.2p 3-Benzotriazol-1-yl-1-(4-bromo-phenyl)-2-
[1,2,4]triazol-1-yl-propan-1-one (19): Eluent petro-
leum/ethyl acetate (1 : 1) as the eluent, Yield 32%,
white solid, mp: 180⋅5 – 182⋅0°С; Anal. Calcd. (%):
C, 51⋅40; H, 3⋅30; N, 21⋅16; Found (%): C, 51⋅26; H,
2.2u 4-Methyl-benzoic acid 1-benzotriazol-1-
ylmethyl-2-(2-methyl-phenyl)-2-oxo-ethyl ester (24):
Eluent acetone, Yield 48%, white solid, m.p.:
117⋅0 – 119⋅5°С; Anal. Calcd. (%): C, 72⋅16; H,
5⋅30; N, 10⋅52; Found (%): C, 72⋅18; H, 5⋅13; N,
–1
–1
3⋅41; N, 20⋅97; IR, νmax/cm (KBr): 1708 (s, C=O),
1585 (C=N); H NMR (CDCl3): 4⋅45, 4⋅54
10⋅46; IR, νmax/cm (KBr): 1720, 1696 (s, C=O),
1
1
1610 (C=N), 1291, 1102 (s, C–O); H NMR
2
3
( J = 14⋅85; 2H, CH2), 5⋅69 ( J = 8⋅4; 1H, CH),
7⋅35–8⋅24 (8H, HAr), 8⋅24, 8⋅46 (2H, HTr).
(CDCl3): 2⋅34–2⋅46 (6H, methyl, CH3), 5⋅44, 5⋅45
2
3
( J = 15; 2H, CH2), 6⋅69 ( J = 8⋅4; 1H, CH), 7⋅22–
7⋅96 (12H, HAr).
2.2q Nicotinic acid 1-benzotriazol-1-ylmethyl-2-
(2-methyl-phenyl)-2-oxo-ethyl ester (20): Eluent
petroleum/ethyl acetate (1 : 1) as the eluent, Yield
39%, pale yellow solid, m.p.: 145⋅5 – 147⋅0°С;
Anal. Calcd. (%): C, 68⋅38; H, 4⋅70; N, 14⋅50;
2.2v 4-Ethyl-benzoic
acid
1-benzotriazol-1-
ylmethyl-2-(2-methyl-phenyl)-2-oxo-ethyl ester (25):
Eluent acetone, Yield 42%, white solid, m.p.:
111⋅2 – 114⋅2°С; Anal. Calcd. (%): C, 72⋅62; H,
5⋅61; N, 10⋅16; Found (%): C, 73⋅09; H, 5⋅83; N,
–1
Found: C, 68⋅18; H, 4⋅65; N, 14⋅44; IR, νmax/cm
(KBr): 1731, 1694 (s, C=O), 1593 (C=N), 1286,
–1
9⋅96; IR, νmax/cm (KBr): 1719, 1697 (s, C=O),
1
1105 (s, C–O); H NMR (CDCl3): 2⋅40 (3H, CH3),
1
1609 (C=N), 1292, 1096 (s, C–O); H NMR (CDCl3):
2
3
5⋅44, 5⋅43 ( J = 15; d, 2H, –CH2–), 6⋅75 ( J = 3⋅7,
3J = 8⋅43; t, 1H, –O–CH–), 7⋅33–8⋅93 (m, 12H, HAr).
1⋅19 (3H, ethyl, CH3), 2⋅45 (3H, methyl, CH3), 2⋅80
(2H, ethyl, CH2), 5⋅45, 5⋅54 ( J = 14⋅75; 2H, CH2),
2
3
6⋅69 ( J = 8⋅5; 1H, CH), 7⋅27–7⋅99 (12H, HAr).
2.2r Isonicotinic acid 1-benzotriazol-1-ylmethyl-2-
(2-methyl phenyl)-2-oxo-ethyl ester (21): Eluent
petroleum/ethyl acetate (2 : 1) as the eluent, Yield
35%, pale yellow solid, m.p.: 143⋅5 – 145⋅0°С;
Anal. Calcd.(%): C, 68⋅38; H, 4⋅70; N, 14⋅50;
2.2w 2-Methyl-benzoic acid 1-benzotriazol-1-
ylmethyl-2-(2-methyl-phenyl)-2-oxo-ethyl ester (26):
ethanol, Yield 43%, white solid, m.p.: 121⋅5 –
123⋅0°С; Anal. Calcd. (%): C, 72⋅16; H, 5⋅30; N,
–1
Found: C, 68⋅10; H, 4⋅98; N, 14⋅69; IR, νmax/cm
(KBr): 1739, 1688 (s, C=O), 1599 (C=N), 1278,
10⋅52; Found (%): C, 72⋅18; H, 5⋅13; N, 10⋅41; IR,
ν
1
–1
max/cm (KBr): 1720, 1693 (s, C=O), 1610 (C=N),
1086 (s, C–O); H NMR (CDCl3): 2⋅50 (3H, CH3),
2
1
5⋅25, 5⋅24 ( J = 14⋅95; d, 2H, –CH2–), 6⋅57
1292, 1101 (s, C–O); H NMR (CDCl3): 2⋅36–2⋅45
(6H, methyl, CH3), 5⋅43, 5⋅45 ( J = 15; 2H, CH2),
3
3
2
( J = 3⋅75, J = 8⋅43; t, 1H, –O–CH–), 7⋅14–8⋅51 (m,
12H, HAr).
3
6⋅69 ( J = 8⋅5; 1H, CH), 7⋅23–7⋅45 (12H, HAr).