Benzoyl chloride, 3-nitro- → HCID 18506156, compound

HRID 1357391Notes

Reaction equation

HRID 1357391 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[C:15]([CH:24]=[CH:25][C:26]=2[C:27]2[N:31]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:30]=[N:29][N:28]=2)[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:39]([C:42]1[CH:43]=[C:44]([CH:48]=[CH:49][CH:50]=1)[C:45](Cl)=[O:46])([O-:41])=[O:40]>CC(C)=O>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[C:15]([CH:24]=[CH:25][C:26]=2[C:27]2[N:31]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:30]=[N:29][N:28]=2)[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:45](=[O:46])[C:44]2[CH:48]=[CH:49][CH:50]=[C:42]([N+:39]([O-:41])=[O:40])[CH:43]=2)=[N:11][N:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 18506136HCID 18506136, compound

Product 1

HCID 18506156HCID 18506156, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-[3,4-Bis-(1-benzyl-1H-tetrazol-5-yl)phenoxy]phenylamine (37 mg, 0.07 mmol) and TEA (19 mg, 0.18 mmol) were mixed in acetone (10 ml), and 3-nitrobenzoyl chloride (15 mg, 0.08 mmol) was added. The reaction mixture was stirred for 120 hours at room temperature. The reaction mixture was evaporated in vacuo to an oil. The oil was purified on a silica column with methylene chloride/methanol (39:1) as eluent. The title compound was isolated as yellow oil (yield: 30 mg (62%). 1H-NMR (CDCl3 in ppm): 5.6 (4H,2xs); 7.0 (1H,d,d); 7.15 (1H,d,d); 7.2 (1H,d,d); 7.25-7.4 (11H,m); 7.6 (1H,d,d); 7.73 (1H,d); 7.9 (1H,d); 8.1 (1H,d,d); 8.35 (1H,d,d); 8.45 (1H,broad s); 8.55 (1H,d,d); 8.7 (1H,d,d).

Workup

  1. customThe reaction mixture was evaporated in vacuo to an oil
  2. customThe oil was purified on a silica column with methylene chloride/methanol (39:1) as eluent

Sources & evidence

ORD record
ord-0027b81ff3764a21913fd50c5502472c
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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