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

HRID 354770
Notes
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Reaction equation

HRID 354770 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.[Br:25]N1C(=O)CCC1=O>Cl.C(O)=O>[Br: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

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 205061515-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 205061919-bromo-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 313Hydrochloric Acid
Solvent

Procedure

30 g (0.092 mol) of 5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 600 ml of concentrated hydrochloric acid and 600 ml of formic acid, treated with 49.5 g of N-bromosuccinimide and stirred at room temperature for 48 hours. Subsequently, an additional 33 g of N-bromosuccinimide are added thereto and the mixture is stirred at room temperature for 4 days. The solution is evaporated and the residue is poured into ice and aqueous ammonia. After extracting the aqueous solution three times with methylene chloride, the organic phase is dried and evaporated. The residue is chromatographed on 2 kg of silica gel with methylene chloride and methylene chloride/ethyl acetate (20:1) as the elution agent. There is obtained 9-bromo-5-(o-fluorophenyl)-1,3-dihydro-3,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one of melting point 164° (ether/n-hexane).

Workup

  1. stirringthe mixture is stirred at room temperature for 4 days
  2. customThe solution is evaporated
  3. additionthe residue is poured into ice and aqueous ammonia
  4. extractionAfter extracting the aqueous solution three times with methylene chloride
  5. customthe organic phase is dried
  6. customevaporated
  7. customThe residue is chromatographed on 2 kg of silica gel with methylene chloride and methylene chloride/ethyl acetate (20:1) as the elution agent

Sources & evidence

ORD record
ord-7e8036f8908c4d0688f34f68f0736d01
Source dataset
uspto-grants-1983_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04377522

Reaction notes

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