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

HRID 2071367
ノート
印刷プレビュー

反応式

HRID 2071367 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])[CH:10]([CH3:23])[N:9]=1.[C:24](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.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])[CH:10]([CH3:23])[N:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6497Dimethyl Sulfate2 回HCID 11430Potassium Carbonate2 回HCID 933645-(2-Chlorophenyl)-3-methyl-7-nitro-1,3-dihydro-2h-1,4-benzodiazepin-2-one

生成物 1

HCID 20443626(+)-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 180
Acetone
溶媒

実験手順

10 g of (+)-5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 100 ml of acetone and treated with 6.3 g of potassium carbonate and 3.5 ml of dimethyl sulphate. After stirring for 2 hours at room temperature, a further 1 g of potassium carbonate and 1 ml of dimethyl sulphate are added, after which the mixture is stirred for a further hour at room temperature. The mixture is treated with 3 ml of glacial acetic acid and the acetone is distilled off. The residue is treated with 10% sodium bicarbonate solution and extracted with methylene chloride. The methylene chloride solution is dried over sodium sulphate, filtered and concentrated. The residue is purified on a column of silica gel (eluant: methylene chloride and methylene chloride/ethyl acetate 10:1) and crystallized from ether/ petroleum ether. There is obtained (+)-5-(o-chlorophenyl)--1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one which melts at 156°-158° C. and exhibits a rotation of [α]25 D =+376.2° (in methylene chloride, 1%).

後処理

  1. stirringafter which the mixture is stirred for a further hour at room temperature
  2. distillationthe acetone is distilled off
  3. additionThe residue is treated with 10% sodium bicarbonate solution
  4. extractionextracted with methylene chloride
  5. dry with materialThe methylene chloride solution is dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified on a column of silica gel (eluant: methylene chloride and methylene chloride/ethyl acetate 10:1)
  9. customcrystallized from ether/ petroleum ether

出典と根拠

ORDレコード
ord-c9fb3d60142e4335a3b5654a0c6eef1f
出典データセット
uspto-grants-1977_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04046890

反応ノート

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