2-Bromo-5-nitrobenzoyl chloride → [2,4-Bis-(2-bromo-4-nitrobenzoylamino)phenoxy]phthalic acid dimethyl ester
Reaction equation
COC(=O)C1C(=CC([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:24]=3[Br:32])=[CH:17][C:16]=2[NH:34][C:35](=[O:46])[C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][C:37]=2[Br:45])=CC=1)C(OC)=O.[CH3:48][O:49][C:50](=[O:70])[C:51]1[C:52](=[CH:57][C:58](OC2C=CC(N)=CC=2N)=[CH:59][CH:60]=1)[C:53]([O:55][CH3:56])=[O:54].BrC1C=CC([N+]([O-])=O)=CC=1C(Cl)=O>>[CH3:56][O:55][C:53](=[O:54])[C:52]1[C:51](=[C:60]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:33])[C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:24]=3[Br:32])=[CH:17][C:16]=2[NH:34][C:35](=[O:46])[C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][C:37]=2[Br:45])[CH:59]=[CH:58][CH:57]=1)[C:50]([O:49][CH3:48])=[O:70]Participants
4
Reactant 3
Product 1
Procedure
4-[2,4-Bis-(2-bromo-4-nitrobenzoylamino)phenoxy]phthalic acid dimethyl ester (Compound 113) from 4-(2,4-diaminophenoxy)phthalic acid dimethyl ester (0.53 g) and 2-bromo-5-nitrobenzoyl chloride (1.0 g). The crude product purified on silica gel column (eluent: methylene chloride:methanol (5:1)) to give 4-([2,4-bis-(2-bromo-4-nitrobenzoylamino)phenoxy]phthalic acid dimethyl ester as brownish crystals (yield: 0.81 g 63%). Mp: 138-142° C. LC/MS: 794 (M+Na), 773 (MH+), 740 (M—OMe). CHN: Calculated: C: 46.66; H: 2.61; N: 7.25; Br: 20.69. Found C: 47.05; H: 2.94; N: 6.85; Br: 20.22.
Workup
- customThe crude product purified on silica gel column (eluent: methylene chloride:methanol (5:1))
Sources & evidence
- ORD record
- ord-e5c8431455ba40839aea2d315a26eed6
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06590118B1
Reaction notes
Loading…