Ammonium Hydroxide → 2-amino-N-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)-2-methylpropanamide

HRID 1772326Notes

Reaction equation

Br[C:2]([CH3:23])([CH3:22])[C:3]([NH:5][C:6]1[S:7][C:8]([CH3:21])=[C:9]([CH3:20])[C:10]=1[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[O:4].[OH-].[NH4+:25]>O1CCCC1>[NH2:25][C:2]([CH3:23])([CH3:22])[C:3]([NH:5][C:6]1[S:7][C:8]([CH3:21])=[C:9]([CH3:20])[C:10]=1[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A round bottomed flask was charged with 2-bromo-N-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)-2-methylpropanamide (5 g, 12.06 mmol) and a stir bar, followed by tetrahydrofuran (25 mL, 0.5 M) and ammonium hydroxide (30%, 7.82 ml, 60.3 mmol, 5 equiv). The solution was stirred at 60° C. 4 h, at which point LC/MS analysis indicated complete consumption of the starting material. The solution was diluted with ethyl acetate, washed successively with water and brine, and purified by column chromatography (eluting with hexanes/ethyl acetate) to yield 2-amino-N-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)-2-methylpropanamide as a yellow amorphous solid (m/z=351), which was used in the subsequent reaction.

Workup

custom4 h
customconsumption of the starting material
additionThe solution was diluted with ethyl acetate
washwashed successively with water and brine
custompurified by column chromatography (eluting with hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-63c0130009344206ac100c059ef48a7b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249161B2

Reaction notes

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