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

反応式

HRID 963037 の反応式
[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

参加物

6

反応物 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 124342995-(2-Chlorophenyl)-7-ethyl-2-hydrazinyl-3H-thieno[2,3-e]-1,4-diazepine

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-62be24d7b7424df099f58b6f3682c35c
出典データセット
uspto-grants-1998_06
特許番号
US05760032

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