Cyclohexanecarbonyl chloride → 4-(2-Chlorophenyl)-9-cyclohexyl-2-ethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

HRID 963037

반응식

HRID 963037 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:19]=[C:18]([CH2:20][CH3:21])[S:17][C:10]=2[N:11]=[C:12]([NH:15][NH2:16])[CH2:13][N:14]=1.[CH:22]1([C:28](Cl)=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:19]=[C:18]([CH2:20][CH3:21])[S:17][C:10]=2[N:11]2[C:28]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:16][N:15]=[C:12]2[CH2:13][N:14]=1

참가 물질

6

반응물 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 124342992-hydrazino-5-o-chlorophenyl-7-ethyl-3H-thieno[2,3-e][1,4]diazepine

생성물 1

HCID 189176634-(2-Chlorophenyl)-9-cyclohexyl-2-ethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine수율 58.2%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 1140Toluene용매HCID 6212Chloroform용매

실험 절차

5-(2-Chlorophenyl)-7-ethyl-2-hydrazino-3H-thieno[2,3-e] [1,4]diazepine (20 g) was suspended in chloroform (200 ml) at room temperature. Cyclohexanecarboxylic acid chloride (10.1 g) was added, and the mixture was stirred for 3 hours. The reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated to give an oil. The oil was dissolved in a mixed solvent of toluene (200 ml) and acetic acid (5.4 ml), and the mixture was refluxed for 3 hours. The reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine and dried over magnesium sulfate. The solvent was evaporated. The residue was purified by silica gel column chromatography (eluted with ethyl acetate), and isopropyl ether was added to give 15 g of 4-(2-chlorophenyl)-9-cyclohexyl-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine.

후처리

  1. washThe reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customto give an oil
  5. temperaturethe mixture was refluxed for 3 hours
  6. washThe reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography (eluted with ethyl acetate), and isopropyl ether
  10. additionwas added

출처 및 근거

ORD 기록
ord-62be24d7b7424df099f58b6f3682c35c
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760032

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