Dichloromethane → rac-7-amino-6,8-dichloro-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

HRID 2199040Notes

Reaction equation

HRID 2199040 reaction equation
[Cl:1]N1C(=O)CCC1=O.[NH2:9][C:10]1C=[CH:12][C:13]2[N:19]([CH3:20])[C:18](=[O:21])[CH:17]([CH3:22])[N:16]=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[C:14]=2[CH:30]=1.[CH2:31]([Cl:33])Cl>C(=O)([O-])[O-].[Na+].[Na+]>[NH2:9][C:10]1[C:31]([Cl:33])=[CH:12][C:13]2[N:19]([CH3:20])[C:18](=[O:21])[CH:17]([CH3:22])[N:16]=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[C:14]=2[C:30]=1[Cl:1]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 31398ChlorosuccinimideHCID 10335749rac-7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 20516782rac-7-amino-6,8-dichloro-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

26.8 g (0.2 mol) of N-chlorosuccinimide are added to a solution, stirred at room temperature, of 30 g (0.095 mol) of rac-7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one in 500 ml of methylene chloride and the mixture is stirred for 65 hours. The mixture is subsequently diluted with 400 ml of methylene chloride, 500 ml of 2 N sodium carbonate solution are added thereto, the phases are separated and the organic phase is washed with water. After drying and removal of the solvent in vacuo, the residue is chromatographed on 1 kg of silica gel using chloroform for the elution. From methylene chloride/cyclohexane there is obtained rac-7-amino-6,8-dichloro-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one of melting point 186°-187° C.

Workup

  1. additionare added
  2. customthe phases are separated
  3. washthe organic phase is washed with water
  4. customAfter drying
  5. customremoval of the solvent in vacuo
  6. customthe residue is chromatographed on 1 kg of silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-2d7848c4d23a4ed5bb4c4f13f378b7f3
Source dataset
uspto-grants-1982_11
Patent number
US04361511

Reaction notes

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