Veratroyl chloride → HCID 9890246, compound

HRID 991428Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[NH2:14][C:15]1[CH:16]=[C:17]([NH:22][C:23](=[O:33])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N+:30]([O-:32])=[O:31])[CH:18]=[CH:19][C:20]=1[Cl:21]>N1C=CC=CC=1>[Cl:21][C:20]1[CH:19]=[CH:18][C:17]([NH:22][C:23](=[O:33])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N+:30]([O-:32])=[O:31])=[CH:16][C:15]=1[NH:14][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3,4-Dimethoxybenzoyl chloride (1.55 g) was added to a stirred mixture of N-(3-amino-4-chlorophenyl)-2-nitrobenzamide (1.5 g) and pyridine (20 ml) and the mixture was stirred and heated to 80° C. for 16 hours. The mixture was cooled to ambient temperature and evaporated. The residue was partitioned between methylene chloride and 1N aqueous hydrochloric acid solution. The organic phase was washed with a saturated aqueous sodium bicarbonate solution and evaporated. The residue was triturated under ethyl acetate. The resultant solid was isolated, washed with a saturated aqueous sodium bicarbonate solution and dried under vacuum at 40° C. There was thus obtained the title compound (1.63 g);

Workup

temperatureThe mixture was cooled to ambient temperature
customevaporated
customThe residue was partitioned between methylene chloride and 1N aqueous hydrochloric acid solution
washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution
customevaporated
customThe residue was triturated under ethyl acetate
customThe resultant solid was isolated
washwashed with a saturated aqueous sodium bicarbonate solution
customdried under vacuum at 40° C

Sources & evidence

ORD record: ord-ad800d48657a4aa3a373fc5aad73b8cb
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465455B1

Reaction notes

Loading…