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

반응식

HRID 981459 반응식
[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

참가 물질

7

반응물 5

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

생성물 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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9afa05ec484447ffa9964d40d620868f
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04992437

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