Ammonia → 7-amino-6,8,9-trichloro-1,3-dihydro-5-(o-fluorophenyl)-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

HRID 354763Notes

Reaction equation

HRID 354763 reaction equation
[NH2:1][C:2]1C=[C:4]([Cl:24])[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[F:22])[C:6]=2[CH:23]=1.[Cl:25]NC(=O)CCC(N)=O.N.[CH2:35]([Cl:37])Cl>>[NH2:1][C:2]1[C:35]([Cl:37])=[C:4]([Cl:24])[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[F:22])[C:6]=2[C:23]=1[Cl:25]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 15238416N-chlorosuccinamideHCID 205061437-amino-9-chloro-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 205061967-amino-6,8,9-trichloro-1,3-dihydro-5-(o-fluorophenyl)-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Procedure

4.75 g (0.014 mol) of 7-amino-9-chloro-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one are dissolved in 100 ml of dry methylene chloride and treated with 4.2 g of N-chlorosuccinamide. The reaction mixture is heated at reflux for 40 hours, treated with 25 percent aqueous ammonia and extracted several times with methylene chloride. After drying and evaporating the organic phase, the residue is chromatographed on 250 g of silica gel with methylene chloride/ethyl acetate (20:1) as the elution agent. There is obtained 7-amino-6,8,9-trichloro-1,3-dihydro-5-(o-fluorophenyl)-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one of melting point 165°-166° (ether/n-hexane).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 40 hours
  3. extractionextracted several times with methylene chloride
  4. customAfter drying
  5. customevaporating the organic phase
  6. customthe residue is chromatographed on 250 g of silica gel with methylene chloride/ethyl acetate (20:1) as the elution agent

Sources & evidence

ORD record
ord-4dbd35921bbf4ba2bc446592765819a2
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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