Thionyl Chloride → 3-Chlorothiophene-2-carbonyl chloride

HRID 581082

반응식

HRID 581082 반응식
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([OH:13])=O>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([Cl:3])=[O:13]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 7012693-Chlorothiophene-2-carboxylic acid

생성물 1

HCID 27358243-Chlorothiophene-2-carbonyl chloride

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Excess thionyl chloride (3.5 ml, 48.0 mmoles) was added to 0.85 g (5.2 mmoles) of 3-chloro-2-thiophenecarboxylic acid (prepared according to Corral, C., et al., Heterocycles 23:1431 (1985)) dissolved in 50 ml of toluene and stirring at room temperature. After addition the solution was refluxed for 3 hours to form 3-chloro-2-thiophenecarbonyl chloride. Concentration of the reaction solution gave the acid chloride as a white solid. The acid chloride was then dissolved in 4 ml of N,N-dimethylformamide and slowly added to a cooled (ice/water bath) stirring solution of 5-chloro-2-oxindole-1-carboxamide (1.0 g, 4.71 mmoles) and 4-(N,N-dimethylamino)pyridine (1.3 g, 10.5 mmoles) in 10 ml of N,N-dimethylformamide. After 45 minutes the solution was allowed to warm to room temperature and after 2 hours was worked-up by pouring into a mixed ice/6N hydrochloric acid solution. A yellow precipitate formed. The precipitate was filtered, washed with water and dried to give 1.3 g of impure product as a yellow solid. Recrystallization with acetic acid/heptane (2:1) gave 0.77 g (2.2 mmoles) of pure title compound as yellow needles, m.p. 222-224° C. Total yield of product was 42%.

후처리

  1. additionAfter addition the solution
  2. temperaturewas refluxed for 3 hours

출처 및 근거

ORD 기록
ord-4f2f07af5b9a4bb68c8c2437d9e484bd
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919809

연결된 노트

불러오는 중…