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2-Thiophenecarbonitrile → HCID 178504800、化合物

HRID 52359
ノート
印刷プレビュー

反応式

HRID 52359 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

HCID 178504800HCID 178504800、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 6212Chloroform溶媒

実験手順

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,

後処理

  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

出典と根拠

ORDレコード
ord-8333f017966a488488ae3ed5b1ad6afd
出典データセット
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05616601

反応ノート

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