Dimethylformamide → HCID 898498, compound

HRID 1084825Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])=[O:9].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:31](I)[CH3:32]>CC(C)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH2:31][CH3:32])=[O:14])=[O:9]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 2-[3-(2-thienyl)acrylamido]benzoic acid (273 mg, 1 mmol) in acetone (2 ml) were added potassium carbonate (194 mg, 1.4 mmol) and dry dimethylformamide (1 ml). To the resulting solution, ethyl iodide (218 mg, 1.4 mmol) and dry dimethylformamide (2 ml) were added and the mixture was stirred at 60° C. for 1 hour. The reaction mixture was poured into ice water. The precipitated solid was collected by suction, and recrystallized from methanol to give pale yellow crystals of the desired compound (197 mg, yield, 65%). m.p., 120°-122° C.

Workup

customThe precipitated solid was collected by suction
customrecrystallized from methanol

Sources & evidence

ORD record: ord-51c3f0397e8f469bb8be3e0dffc61165
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05006548

Reaction notes

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