Benzoyl chloride → N-(2-(thiophen-3-yl)ethyl)benzamide

HRID 2267475Notes

Reaction equation

Cl.[S:2]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH2:9])=[CH:3]1.C(N(CC)CC)C.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[S:2]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH:9][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(Thiophen-3-yl)ethanamine hydrochloride (3 g, 18 mmol) was taken in THF (40 mL) and treated with triethylamine (9.92 mL, 71.2 mmol). The reaction was cooled down to 0° C. and benzoyl chloride (2.55 mL, 21.9 mmol), diluted with THF was added dropwise to the reaction. The reaction was stirred for 3 h and the volatiles removed in vacuo. The residue was dissolved in ethyl acetate and washed with an aqueous saturated solution of sodium bicarbonate, water and brine. The organic solution was dried with sodium sulfate and purified by flash chromatography using a gradient of 25 to 70% ethyl acetate in hexanes to afford an off-white solid (4 g). MS (M+H)+ 232.

Workup

additionwas added dropwise to the reaction
customthe volatiles removed in vacuo
dissolutionThe residue was dissolved in ethyl acetate
washwashed with an aqueous saturated solution of sodium bicarbonate, water and brine
dry with materialThe organic solution was dried with sodium sulfate
custompurified by flash chromatography

Sources & evidence

ORD record: ord-b24ff8e5f98c48cf80f6b18c53d4186a
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Reaction notes

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