Thioacetamide → 5,6-Dihydro-2-methyl-6-(4-nitrobenzoyl)-4H-thiazolo[5,4-d] [1]benzazepine

HRID 355876노트

반응식

HRID 355876 반응식
Br[CH:2]1[C:8](=O)[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:4][CH2:3]1.[C:25]([NH2:28])(=[S:27])[CH3:26]>C(O)C>[CH3:26][C:25]1[S:27][C:2]2[CH2:3][CH2:4][N:5]([C:14](=[O:24])[C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)[C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=3[C:8]=2[N:28]=1

참가 물질

4

반응물 2

HCID 2723949ThioacetamideHCID 540926514-bromo-1-(4-nitrobenzoyl)-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

생성물 1

HCID 867515725,6-Dihydro-2-methyl-6-(4-nitrobenzoyl)-4H-thiazolo[5,4-d] [1]benzazepine수율 96.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 1.19 g of 4-bromo-1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepin-5-one and 0.230 g of thioacetamide in 4 ml of ethyl alcohol is refluxed under argon for 18 hours. The volatiles are evaporated in vacuo to a residue which is partitioned between CHCl3 and 10% NaHCO3. The organic layer is separated and washed twice with water. The organic layer is separated, dried (MgSO4) and evaporated in vacuo to give 1.08 g of yellow foam which is purified by flash chromatography on silica by elution with 4% ethyl acetate in methylene chloride to give 560 mg of the desired product as pale yellow foam.

후처리

  1. temperatureis refluxed under argon for 18 hours
  2. customThe volatiles are evaporated in vacuo to a residue which
  3. customis partitioned between CHCl3 and 10% NaHCO3
  4. customThe organic layer is separated
  5. washwashed twice with water
  6. customThe organic layer is separated
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-60a46f6ddc7f4590b6a45e21ce5f1d7e
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834461

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