Chlorine → 7-amino-6-chloro-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

HRID 354747Notes

Reaction equation

HRID 354747 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:6]=2[CH:23]=1.[Cl:24]Cl>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:6]=2[C:23]=1[Cl:24]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 205061787-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 205061507-amino-6-chloro-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

17 g (0.052 mol) of 7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one in 100 ml of glacial acetic acid are treated slowly with a solution of 4 g of chlorine gas in 50 ml of glacial acetic acid. The reaction mixture is stirred at room temperature, evaporated after 60 minutes and the residue is treated with aqueous ammonia and methylene chloride. After extracting the aqueous phase with methylene chloride, the organic extract is dried and evaporated. The crude product is purified by chromatography on 600 g of silica gel with methylene chloride and methylene chloride/ethyl acetate (5:1) as the elution agent. From ethyl acetate/ether/n-hexane there is obtained 7-amino-6-chloro-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one of melting point 195°-196°.

Workup

  1. customevaporated after 60 minutes
  2. additionthe residue is treated with aqueous ammonia and methylene chloride
  3. extractionAfter extracting the aqueous phase with methylene chloride
  4. extractionthe organic extract
  5. customis dried
  6. customevaporated
  7. customThe crude product is purified by chromatography on 600 g of silica gel with methylene chloride and methylene chloride/ethyl acetate (5:1) as the elution agent

Sources & evidence

ORD record
ord-126f32c10a284008a3bc107ff869f7ff
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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