Niclosamide → 4-Chloro-2-(2-chloro-4-nitrophenylcarbamoyl)phenyl benzoate

HRID 1914487

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[Cl:19])=[O:8].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:22]([O:21][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][C:6]=1[C:7](=[O:8])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[Cl:19])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide (1.27 g., 3.88 mmol) in pyridine (15 mL) was treated with 4-dimethylaminopyridine (30 mg) and benzoyl chloride (0.49 mL, 4.27 mmol) was introduced dropwise. The suspension was warmed to 50° C. for one hour then cooled to room temperature and stirred for 17 hours. The reaction mixture was partitioned between 1N aqueous HCl and ethyl acetate. The ethyl acetate phase was washed with water, then brine, dried over magnesium sulfate, and concentrated to an off-white solid. This was recrystallized from ethyl acetate/hexanes. 1HNMR (500 MHz, DMSO-d6): δ7.70 (M, 3H), 7.73 (m, 2H), 7.89 (m, 1H), 7.93 (M, 1H), 8.19 (m, 1H), 8.32 (m, 1H), 10.60 (s, 1H).

Workup

additionwas introduced dropwise
temperaturethen cooled to room temperature
customThe reaction mixture was partitioned between 1N aqueous HCl and ethyl acetate
washThe ethyl acetate phase was washed with water
dry with materialbrine, dried over magnesium sulfate
concentrationconcentrated to an off-white solid
customThis was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-ff01bf9a2af444e6adce3addbdef6caf
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614205B2

Linked notes

Loading…