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

HRID 354740Notes

Reaction equation

HRID 354740 reaction equation
[Cl:1]Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([CH3:17])([CH3:16])[N:10]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:8]=2[CH:25]=1>Cl>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([CH3:17])([CH3:16])[N:10]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:8]=2[C:25]=1[Cl:1]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 205061627-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 205061857-amino-6-chloro-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Chlorine gas is conducted slowly at between -5° and 0° through a solution of 6 g (0.019 mol) of 7-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one in 70 ml of concentrated hydrochloric acid until the starting material has almost completely been consumed. The reaction mixture is poured into a mixture of ice and soda solution, whereupon it is extracted with methylene chloride and the extract is dried and evaporated. The residue is chromatographed on 300 g of silica gel with methylene chloride/ethyl acetate (10:1) as the elution agent. From ether-petroleum ether there is obtained 7-amino-6-chloro-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one of melting point 192°-193°.

Workup

  1. customhas almost completely been consumed
  2. additionThe reaction mixture is poured into a mixture of ice and soda solution, whereupon it
  3. extractionis extracted with methylene chloride
  4. customthe extract is dried
  5. customevaporated
  6. customThe residue is chromatographed on 300 g of silica gel with methylene chloride/ethyl acetate (10:1) as the elution agent

Sources & evidence

ORD record
ord-67d90ddc195b485b93503d61590dafb3
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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