Acetic Acid → (S)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

HRID 1632169ノート

反応式

HRID 1632169 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[NH:12][C:11](=[O:22])[C@H:10]([CH3:23])[N:9]=1.[C:24](=O)([O-])[O-].[K+].[K+].CI.C(O)(=O)C>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=2[N:12]([CH3:24])[C:11](=[O:22])[C@H:10]([CH3:23])[N:9]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3033985Meclonazepam

生成物 1

HCID 54101851(S)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

100 g (0.3 mol) of (S)-5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 700 ml of dry acetone. The solution is treated with 79 ml of ground potassium carbonate and with 31.4 ml of methyl iodide and the mixture is stirred at room temperature for 4 hours. The mixture is treated with 30 ml of glacial acetic acid and evaporated. The residue is treated with an ice/water mixture and extracted several times with methylene chloride. The organic phase is washed with water, dried over sodium sulphate, concentrated and treated with methanol. After filtering off the separated crystals, there is obtained (S)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 159°; [α]25D =+381.2° (1 percent solution in methylene chloride).

後処理

  1. customevaporated
  2. additionThe residue is treated with an ice/water mixture
  3. extractionextracted several times with methylene chloride
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. additiontreated with methanol
  8. filtrationAfter filtering off the separated crystals

出典と根拠

ORDレコード
ord-ca2b3ea5030b46fa9b4bb9ecb07b544a
出典データセット
uspto-grants-1984_10
特許番号
US04474777

反応ノート

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