반응 #7054

반응 방정식

carbon monoxide

5-bromothiophene-2-sulfonamide

triethyl amine

1,3-bis(diphenylphosphino) propane

ethyl acetate

→

title compound

5-(Methoxycarbonyl)thiophene-2-sulfonamide

용매

methanol

dimethylformamide

brine

반응 조건

후처리

1. 1
   기타The organic phase is separated
2. 2
   추출the aqueous layer is extracted with 10 mL ethyl acetate
3. 3
   건조The combined organic layers are dried over sodium sulfate
4. 4
   농축concentrated in vacuo
5. 5
   기타chromatographed on silica (0–1% methyl alcohol in methylene chloride)

실험 절차

A mixture of 5-bromothiophene-2-sulfonamide (0.50 g, 2.1 mmol), triethyl amine (1 mL), methanol (1 mL), palladium acetate (0.046 g, 2.1 mmol) and 1,3-bis(diphenylphosphino) propane (0.085 g, 2.1 mmol) (addition in that order) in dimethylformamide (5 mL, anhydrous) is saturated with carbon monoxide gas, at room temperature. This reaction mixture is heated to 100° C. and stirred overnight, under a carbon monoxide atmosphere. 10 mL of brine and 10 mL of ethyl acetate are added to the reaction mixture. The organic phase is separated and the aqueous layer is extracted with 10 mL ethyl acetate. The combined organic layers are dried over sodium sulfate, concentrated in vacuo, and then chromatographed on silica (0–1% methyl alcohol in methylene chloride) to give the title compound, as a yellow solid (0.15 g, 34% yield).

출처