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Chlorine → 9-chloro-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

HRID 354750
Notes
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Reaction equation

HRID 354750 reaction equation
[F: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])[C:10]([CH3:24])([CH3:23])[N:9]=1.[Cl:25]Cl>Cl.C(O)=O.ClCCCl>[Cl:25][C:18]1[C:13]2[NH:12][C:11](=[O:22])[C:10]([CH3:24])([CH3:23])[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C:14]=2[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 24526Chlorine3×HCID 205061515-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 205061649-chloro-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent3×HCID 284
Formic Acid
Solvent
HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 160 g (0.49 mol) of 5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one in 400 ml of concentrated hydrochloric acid and 400 ml of formic acid is treated while stirring with a solution of 46 g of chlorine gas in 400 ml of 1,2-dichloroethane. The reaction mixture, which consists of two phases, is stirred at room temperature, whereby after 3 days a further 25 g of chlorine gas in 200 ml of 1,2-dichloroethane are added and after 5 days a further 5 g of chlorine gas in 40 ml of 1,2-dichloroethane are added. After 7 days, the mixture is concentrated, treated with ice-water, made alkaline with aqueous ammonia and extracted four times with methylene chloride. The organic extract is concentrated and treated with 600 ml of isopropanol. Subsequently, the residual methylene chloride is removed on a steam-bath and the product is left to crystallise. There is obtained 9-chloro-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 174°-175°.

Workup

  1. additionare added
  2. concentrationthe mixture is concentrated
  3. additiontreated with ice-water
  4. extractionextracted four times with methylene chloride
  5. extractionThe organic extract
  6. concentrationis concentrated
  7. additiontreated with 600 ml of isopropanol
  8. customSubsequently, the residual methylene chloride is removed on a steam-bath
  9. waitthe product is left
  10. customto crystallise

Sources & evidence

ORD record
ord-ed0367736b9946b9bb0953a2a941fc68
Source dataset
uspto-grants-1983_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04377522

Reaction notes

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