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2-Thiophenecarbonitrile → HCID 178504800, 화합물

HRID 52359
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HRID 52359 반응식
[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C[Al](C)C.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]#[N:22]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:21]([C:17]2[S:16][CH:20]=[CH:19][CH:18]=2)=[NH:22])=[CH:7][CH:6]=1)(=[O:3])=[O:4]
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참가 물질

6

반응물 3

HCID 660872-ThiophenecarbonitrileHCID 796174-(Methylsulfonyl)anilineHCID 16682925Trimethylaluminum

생성물 1

HCID 178504800HCID 178504800, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 6212Chloroform용매

실험 절차

To a suspension of 4-(methylsulfonyl)aniline (10.4 g, 61.1 mmol) in toluene (400 ml) at 0° C., trimethylaluminum (2M solution in toluene, 46.8 ml, 91.6 mmol) was added over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 2 hours. A solution of 2-thiophenecarbonitrile (10.0 g, 91.6 mmol) in toluene (200 ml) was added over 10 minutes and the mixture was heated to 80°-85° C. After 16 hours, the reaction mixture was cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue was washed with a mixture of methylene chloride/methanol and later with methanol. The combined filtrates were concentrated and the resulting yellow solid was stirred with ethyl acetate and filtered. The pale yellow solid (9.8 g, 57%) was used in the next reaction without further purification: m.p. (DSC) 182° C. Anal. Calc'd. for C12H12N2S2O2 : C, 51.41, H, 4.31, N, 9.99, S, 22.87 Found C, 51.02, H, 4.37, N, 9.80, S, 22.93,

후처리

  1. temperaturethe mixture was heated to 80°-85° C
  2. waitAfter 16 hours
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationAfter filtration
  5. washthe residue was washed with a mixture of methylene chloride/methanol and later with methanol
  6. concentrationThe combined filtrates were concentrated
  7. stirringthe resulting yellow solid was stirred with ethyl acetate
  8. filtrationfiltered
  9. customThe pale yellow solid (9.8 g, 57%) was used in the next reaction without further purification

출처 및 근거

ORD 기록
ord-8333f017966a488488ae3ed5b1ad6afd
출처 데이터셋
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05616601

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