Sodium hydride → 2-(1H-benzimidazol-2-ylsulfanyl)-thiazole-5-carbaldehyde

HRID 1696639

반응식

HRID 1696639 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[S:10].[H-].[Na+].Cl[C:14]1[S:15][C:16]([CH:19]=[O:20])=[CH:17][N:18]=1>O1CCCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:14]1[S:15][C:16]([CH:19]=[O:20])=[CH:17][N:18]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 7070352-MercaptobenzimidazoleHCID 14797652-Chloro-1,3-thiazole-5-carbaldehyde

생성물 1

HCID 598257462-(1H-benzimidazol-2-ylsulfanyl)-thiazole-5-carbaldehyde수율 70.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1,3-Dihydro-benzimidazole-2-thione (1.0 g, 6.66 mmol) is suspended into 50 mL of tetrahydrofuran under argon. Then, 479 mg (9.99 mmol) of sodium hydride is added. The reaction mixture is stirred at room temperature until gas evolution has ceased. 2-Chloro-1,3-thiazole-5-carbaldehyde (983 mg, 6.66 mmol) is then added and the reaction mixture is stirred at room temperature for 2 h, upon which it is filtered. The solid is washed with tetrahydrofuran and dried under reduced pressure. The residue is diluted with water and extracted twice with ethyl acetate and once with dichloromethane. The organic extracts are combined, dried on magnesium sulfate, filtered and concentrated under reduced pressure. 1.23 g of 2-(1H-benzimidazol-2-ylsulfanyl)-thiazole-5-carbaldehyde is obtained as a pale yellow powder. mp: 188° C.

후처리

  1. stirringthe reaction mixture is stirred at room temperature for 2 h, upon which it
  2. filtrationis filtered
  3. washThe solid is washed with tetrahydrofuran
  4. customdried under reduced pressure
  5. additionThe residue is diluted with water
  6. extractionextracted twice with ethyl acetate and once with dichloromethane
  7. customdried on magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8774921c530b4d5aabd29eb07c113f19
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163768B2

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