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

HRID 354742Notes

Reaction equation

HRID 354742 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[F:22])[C:6]=2[CH:23]=1.[Br:24]Br>Br>[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[F:22])[C:6]=2[C:23]=1[Br:24]

Participants

4

Reactant 2

HCID 24408BromineHCID 205061627-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 205061637-amino-6-bromo-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

6.6 g (0.021 mol) of 7-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one, dissolved in 50 ml of concentrated aqueous hydrobromic acid, are treated slowly at between 0° and 5° with 1.2 l of bromine and stirred at 0° for 1 hour. Subsequently, the reaction mixture is poured into a mixture of ice and soda solution, extracted with methylene chloride and the organic extract is evaporated. The residue is purified on 300 g of silica gel with methylene chloride/ethyl acetate (20:1). From ethyl acetate/ether there is obtained 7-amino-6-bromo-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one of melting point 217°-220°.

Workup

  1. additionSubsequently, the reaction mixture is poured into a mixture of ice and soda solution
  2. extractionextracted with methylene chloride
  3. extractionthe organic extract
  4. customis evaporated
  5. customThe residue is purified on 300 g of silica gel with methylene chloride/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-fdbee38c56a64c75af4c4ba4b2b344af
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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