Nordiazepam → Diazepam

HRID 262943

反応式

HRID 262943 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.Cl[CH2:21]Cl.[OH-].[Na+].S(OC)(OC)(=O)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:21])[C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

参加物

6

反応物 4

HCID 2997NordiazepamHCID 6344DichloromethaneHCID 6497Dimethyl Sulfate2 回HCID 14798Sodium Hydroxide

生成物 1

HCID 3016Diazepam

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Dissolve 5.4 g. (0.02 moles) of 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (e.g. product of Example 3) in 35 ml. of dichloromethane and add to this solution 1.2 g. of NaOH (1.5 moles) dissolved in 17 ml. of water. Cool the mixture with good agitation to 0° C. and add slowly 3.8 g. (0.03 moles) of dimethyl sulfate with good cooling and stirring. After all the dimethyl sulfate is added remove the cooling bath and continue stirring for an additional 2 hours. Add water and methylene chloride to the reaction mixture. Separate the layers and wash the methylene chloride layers with water. Dry the organic solution over anhydrous sodium sulfate and evaporate. After recrystallization, 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one is obtained which after drying under vacuum at 110° C. shows a melting point of 129.5°-130.5° (corr.) and no depression on mixed melt with an authentic sample.

後処理

  1. dissolutionDissolve 5.4 g
  2. additionadd slowly 3.8 g
  3. customremove the cooling bath
  4. stirringcontinue stirring for an additional 2 hours
  5. customSeparate the layers
  6. washwash the methylene chloride layers with water
  7. dry with materialDry the organic solution over anhydrous sodium sulfate
  8. customevaporate
  9. customAfter recrystallization

出典と根拠

ORDレコード
ord-7d297480434146ad9f723c4e39808ed7
出典データセット
uspto-grants-1979_05
特許番号
US04155904

関連ノート

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