Alprazolam → U 43465F

HRID 616658

反応式

HRID 616658 の反応式
[CH3:1][N:2]([CH2:4]N(C)C)[CH3:3].C(Cl)(=O)C.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[N:22]3[C:23]([CH3:26])=[N:24][N:25]=[C:21]3[CH2:20][N:19]=[C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:17]=2[CH:33]=1.C(=O)(O)[O-].[Na+].[C:39]1([CH3:49])[CH:44]=[CH:43][C:42]([S:45]([OH:48])(=[O:47])=[O:46])=[CH:41][CH:40]=1>CN(C)C=O.C(O)C>[C:39]1([CH3:49])[CH:40]=[CH:41][C:42]([S:45]([OH:48])(=[O:46])=[O:47])=[CH:43][CH:44]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]2[N:22]3[C:23]([CH2:26][CH2:1][N:2]([CH3:4])[CH3:3])=[N:24][N:25]=[C:21]3[CH2:20][N:19]=[C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:17]=2[CH:33]=1

参加物

8

反応物 5

HCID 2118AlprazolamHCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6101p-Toluenesulfonic acidHCID 6367Acetyl chlorideHCID 516892Sodium Bicarbonate

生成物 1

HCID 134388U 43465F収率 64.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

A stirred solution of N,N,N',N'-tetramethyldiaminomethane (2.244 g., 0.022 mole) in dry dimethylformamide (50 ml.) was cooled in an ice bath and treated dropwise with acetyl chloride (1.65 ml., 0.023 mole). The ice bath was removed and the mixture was kept at 25° for 45 min. and treated with 8-chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine (3.09 g., 0.01 mole). After 30 min. the mixture was poured into ice water, made alkaline with sodium bicarbonate, saturated with sodium chloride and extracted with chloroform. The extract was washed with a dilute salt solution, dried over anhydrous sodium sulfate and concentrated in vacuo using xylene and toluene to help remove residual dimethylformamide. A solution of the residue in ethanol was acidified with a solution of one equivalent of p-toluenesulfonic acid in ethanol and crystallized to give 8-chloro-1-[2-(dimethylamino)ethyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine p-toluenesulfonate in three crops; 2.69 g. of melting point 195°-196° C.; 0.751 g. of melting point 192°-195.5° C. and 0.033 g. of melting point 195°-197° C. The total yield was 64.6%.

後処理

  1. customThe ice bath was removed
  2. extractionsaturated with sodium chloride and extracted with chloroform
  3. washThe extract was washed with a dilute salt solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto help remove residual dimethylformamide
  7. customcrystallized

出典と根拠

ORDレコード
ord-ea8ae3a6a41b4f1e826b97805378de71
出典データセット
uspto-grants-1978_02
特許番号
US04075221

関連ノート

読み込み中…