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

HRID 981459

反応式

HRID 981459 の反応式
[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[C:22]2[CH:23]=[C:24]([CH2:26][CH3:27])[S:25][C:21]=2[N:20]2[C:28]([CH3:31])=[N:29][N:30]=[C:19]2[CH2:18][N:17]=1.[H-].[Na+].[H][H].[N+:36](C1C=C([N+]([O-])=O)C=CC=1ON)([O-])=O>C(O)(=O)C>[NH2:36][C:18]1([C:1]([O:5][CH2:6][CH3:7])=[O:8])[N:17]=[C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[Cl:9])[C:22]2[CH:23]=[C:24]([CH2:26][CH3:27])[S:25][C:21]=2[N:20]2[C:28]([CH3:31])=[N:29][N:30]=[C:19]12

参加物

7

反応物 5

HCID 3307EtizolamHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 87140O-(2,4-dinitrophenyl)hydroxylamineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 15662236ethyl 6-amino-4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine-6-carboxylate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
20 °C

実験手順

To 500 ml of diethyl carbonate were added 22.0 g of 4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine and 4.3 g of sodium hydride, and the mixture was heated. Hydrogen gas began to generate at about 100° C., while the solution gradually colored violet. After 30 minutes' reflux, the mixture was cooled to 20° C., whereto 16.0 g of O-(2,4-dinitrophenyl)hydroxylamine was added. The mixture was stirred for 2 hours. After the completion of the reaction, the reaction mixture was poured into ice-water containing 6 ml of acetic acid. The diethyl carbonate layer was separated, washed twice with water and dried over anhydrous magnesium sulfate. Diethyl carbonate was distilled off under reduced pressure, and diisopropyl ether was added to the obtained residue to separate crystals, which were collected by filtration. The crystals were recrystallized from ethyl acetate to give 18.2 g of ethyl 6-amino-4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine-6-carboxylate, m.p. 180°-181° C.

後処理

  1. temperaturethe mixture was heated
  2. customto generate at about 100° C., while the solution
  3. temperatureAfter 30 minutes' reflux
  4. customAfter the completion of the reaction
  5. customThe diethyl carbonate layer was separated
  6. washwashed twice with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationDiethyl carbonate was distilled off under reduced pressure, and diisopropyl ether
  9. additionwas added to the obtained residue
  10. customto separate crystals, which
  11. filtrationwere collected by filtration
  12. customThe crystals were recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-9afa05ec484447ffa9964d40d620868f
出典データセット
uspto-grants-1991_02
特許番号
US04992437

関連ノート

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