10,11-Dihydro-5h-dibenzo[b,e][1,4]diazepine → 5,11-Dihydro-10-[4-(2-thienyl)benzoyl]-10H-dibenz[b,e][1,4]diazepine

HRID 1457707

반응식

HRID 1457707 반응식
[CH:1]1[C:11]2[CH2:10][NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>ClCCl.C(Cl)(Cl)Cl>[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30]1[CH:38]=[CH:37][C:33]([C:34]([N:9]2[CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[NH:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]2=3)=[O:35])=[CH:32][CH:31]=1

참가 물질

6

반응물 3

HCID 3604610,11-Dihydro-5h-dibenzo[b,e][1,4]diazepineHCID 81531DiisopropylethylamineHCID 27763314-(2-Thienyl)Benzoyl Chloride

생성물 1

HCID 220995695,11-Dihydro-10-[4-(2-thienyl)benzoyl]-10H-dibenz[b,e][1,4]diazepine수율 46.2%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매2회

실험 절차

A mixture of 3 g of 4-(2-thienyl)benzoic acid and 30 ml of sulfonyl chloride is refluxed for 45 minutes and the solvent removed. The residue is dissolved in carbon tetrachloride and the solvent removed under vacuum (2-times) to give 4-(2-thienyl) benzoyl chloride. To a cooled (0° C.) solution of 2.0 g of 5,11-dihydro-10H-dibenz[b,e][1,4]diazepine and 7 ml of N,N-diisopropylethylamine in 30 ml of dichloromethane is added dropwise a solution of 3.15 g of 4-(2-thienyl)benzoyl chloride in 30 ml of dichloromethane. The mixture is stirred at room temperature for 16 hours and diluted with 50 ml of chloroform. The solution is washed with 30 ml each of water, 2N HCl, saturated NaHCO3, water and dried (Na2 SO4). The solvent is removed under vacuum and the residue (3.1 g) chromatographed on silica gel (column) with hexane-ethyl acetate (2:1) as eluent to give 1.8 g of solid, m.p. 114° C.-116° C.

후처리

  1. washThe solution is washed with 30 ml each of water, 2N HCl, saturated NaHCO3, water
  2. customdried (Na2 SO4)
  3. customThe solvent is removed under vacuum
  4. customthe residue (3.1 g) chromatographed on silica gel (column) with hexane-ethyl acetate (2:1) as eluent

출처 및 근거

ORD 기록
ord-0ca780a7b03f4b6886c8c9a7bb8e5ed2
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849735

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