Ethanol → 8-chloro-1-methyl-6-phenyl-3,3a,4,6-tetrahydro-5H-imidazo[1,5-a][1,5]benzodiazepin-5-one

HRID 1763250ノート

反応式

HRID 1763250 の反応式
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7](=[CH:18][N+:19]([O-])=O)[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[CH2:24](O)[CH3:25]>CN(C)C=O.[Ni]>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]3[C:24]([CH3:25])=[N:19][CH2:18][CH:7]3[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

参加物

5

反応物 2

HCID 702EthanolHCID 706056287-Chloro-5-phenyl-1,2,3,4-tetrahydro-2-nitromethylene-5H-1, 5-benzodiazepin-4-one

生成物 1

HCID 227495508-chloro-1-methyl-6-phenyl-3,3a,4,6-tetrahydro-5H-imidazo[1,5-a][1,5]benzodiazepin-5-one

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 6228Dimethylformamide溶媒

実験手順

7-Chloro-5-phenyl-1,2,3,4-tetrahydro-2-nitromethylene-5H-1,5-benzodiazepin-4-one 18.3 g (0.055 mole) was dissolved in 300 ml of dimethylformamide by gentle heating on a steam bath. The solution was cooled to room temperature and 400 ml of ethanol and 55 g of Raney nickel were added. The mixture was hydrogenated at atmospheric pressure for 21 hours. The catalyst was filtered off and washed well with tetrahydrofuran and methylene chloride. The filtrate was evaporated and the residue was dissolved in 325 ml of xylene, and 40 ml of triethyl orthoacetate was added to the solution which was then refluxed for 1 hour. The mixture was evaporated and the residue was crystallized from ethyl acetate to yield end product with mp 248°-251°. The analytical sample was recrystallized from methylene chloride/ethyl acetate to give colorless crystals with mp 250°-252°.

後処理

  1. temperatureby gentle heating on a steam bath
  2. filtrationThe catalyst was filtered off
  3. washwashed well with tetrahydrofuran and methylene chloride
  4. customThe filtrate was evaporated
  5. dissolutionthe residue was dissolved in 325 ml of xylene
  6. addition40 ml of triethyl orthoacetate was added to the solution which
  7. temperaturewas then refluxed for 1 hour
  8. customThe mixture was evaporated
  9. customthe residue was crystallized from ethyl acetate
  10. customto yield end product with mp 248°-251°
  11. customThe analytical sample was recrystallized from methylene chloride/ethyl acetate
  12. customto give colorless crystals with mp 250°-252°

出典と根拠

ORDレコード
ord-4a7cb66ca1234079bc9a038b7f0829c5
出典データセット
uspto-grants-1978_09
特許番号
US04111931

反応ノート

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