Diethyl Ether → 2-[3-(2,2,2-Trichloro-ethanoyl)-ureido]-thiophene-3-carboxylic Acid Amide

HRID 2223356Notes

Reaction equation

[Cl:1][C:2]([Cl:9])([Cl:8])[C:3]([N:5]=[C:6]=[O:7])=[O:4].[NH2:10][C:11]1[S:12][CH:13]=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17].C(OCC)C>N1C=CC=CC=1>[Cl:1][C:2]([Cl:9])([Cl:8])[C:3]([NH:5][C:6](=[O:7])[NH:10][C:11]1[S:12][CH:13]=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Trichloroacetyl isocyanate (10 g, 53 mmol) was added dropwise to the solution of 2-amino-thiophene-3-carboxylic acid amide (3.8 g, 26.5 mmol) in pyridine (110 mL) at 0° C. The resulting reaction mixture was stirred at 0° C. The temperature of the reaction mixture was raised to room temperature over a 3 h period until LC-MS showed no remaining starting material. Diethyl ether (100 mL) was added to the reaction mixture and the resulting precipitate was filtered and dried under vacuum to give the above titled compound as a light grey solid (8.7 g, 26.3 mmol, 99% yield).

Workup

customThe resulting reaction mixture
temperatureThe temperature of the reaction mixture was raised to room temperature over a 3 h period until LC-MS
filtrationthe resulting precipitate was filtered
customdried under vacuum

Sources & evidence

ORD record: ord-aa7231b6575b4498bd84356bf824a5d0
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375131B2

Reaction notes

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