Hydrochloric Acid → ethyl 4-(2-chlorophenyl)-6-(2-ethoxycarbonylethyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine-6-carboxylate

HRID 963098

반응식

HRID 963098 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH2:10][N:9]=1.[H-].[Na+].[C:26](=O)([O:30]CC)[O:27][CH2:28][CH3:29].[C:34]([O:38][CH2:39][CH3:40])(=[O:37])[CH:35]=[CH2:36].Cl>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[C:10]([CH2:36][CH2:35][C:34]([O:38][CH2:39][CH3:40])=[O:37])([C:26]([O:27][CH2:28][CH3:29])=[O:30])[N:9]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 3307EtizolamHCID 7766Diethyl CarbonateHCID 8821Ethyl AcrylateHCID 24758Sodium hydride

생성물 1

HCID 67727783ethyl 4-(2-chlorophenyl)-6-(2-ethoxycarbonylethyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine-6-carboxylate

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

4-(2-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (10.0 g) and 60% sodium hydride (2.0 g) were added to diethyl carbonate (150 ml), and the mixture was refluxed under heating under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to 50° C. Ethyl acrylate (5.37 ml) was added and the mixture was further stirred for 3 hours. The reaction mixture was added to water. 1M Hydrochloric acid was added with vigorous stirring to adjust the aqueous solution to pH 4. The solution was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogencarbonate solution and brine, and dried over magnesium sulfate. The residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-hexane) to give 3.2 g of ethyl 4-(2-chlorophenyl)-6-(2-ethoxycarbonylethyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine-6-carboxylate.

후처리

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating under a nitrogen atmosphere for 2 hours
  3. stirringwith vigorous stirring
  4. extractionThe solution was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous sodium hydrogencarbonate solution and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe residue was purified by silica gel column chromatography (developing solvent:ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-1eaf31c0f4f34a4583d90123ac06bc04
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760032

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