Chloroacetic anhydride → 7-Chloro-3-(5-chloromethyl-[1,2,4]oxadiazol-3-yl)-5-methyl-4,5-dihydro-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1378147ノート

反応式

HRID 1378147 の反応式
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[N:18][OH:19])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:22][CH2:23][C:24](OC(=O)CCl)=O>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]([CH3:20])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:17]=[C:24]([CH2:23][Cl:22])[O:19][N:18]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 10946Chloroacetic anhydrideHCID 541588047-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

生成物 1

HCID 224621917-Chloro-3-(5-chloromethyl-[1,2,4]oxadiazol-3-yl)-5-methyl-4,5-dihydro-imidazo[1,5-a][1,4]benzodiazepin-6-one収率 65%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

9.8 g (32 mmol) of 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime were stirred in 60 ml of N,N-dimethylformamide with 7 g (41 mmol) of chloroacetic anhydride at room temperature for 1 hour and at 105° for 4 hours. After evaporating the solvent the residue was dissolved in methylene chloride and the solution was washed with saturated sodium bicarbonate solution and dried over magnesium sulfate. By evaporation of the solvent and chromatography of the residue on silica gel while eluting with ethyl acetate there were obtained 6.63 g (65%) of 7-chloro-3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-6-one.

後処理

  1. customAfter evaporating the solvent the residue
  2. dissolutionwas dissolved in methylene chloride
  3. washthe solution was washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customBy evaporation of the solvent and chromatography of the residue on silica gel
  6. washwhile eluting with ethyl acetate

出典と根拠

ORDレコード
ord-57e0db0a84dd4197a4af1631fa09a7e7
出典データセット
uspto-grants-1997_09
特許番号
US05665718

反応ノート

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