Bromine → HCID 20562365, compound

HRID 848133Notes

Reaction equation

HRID 848133 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([CH2:14][CH3:15])[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>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([CH2:14][CH3:15])[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 24408Bromine2×HCID 20562360HCID 20562360, compound

Product 1

HCID 20562365HCID 20562365, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

9.3 g (0.03 M) of rac-7-amino-3-ethyl-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one are dissolved in 80 ml of glacial acetic acid. The solution is cooled to 10° C., treated dropwise with 5 g (1.62 ml) of bromine, stirred at 10° C. for a further 10 minutes after the addition of bromine and then concentrated. The residue is treated with a mixture of ice and 10% sodium bicarbonate solution, extracted with methylene chloride and the extract is dried over sodium sulphate, filtered and concentrated. The residual oil is purified on a 200 g silica gel column with methylene chloride/ethyl acetate (10:1) and crystallised from ether. There is obtained rac-7-amino-3-ethyl-6-bromo-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one which melts at 248° C.

Workup

  1. concentrationconcentrated
  2. additionThe residue is treated with a mixture of ice and 10% sodium bicarbonate solution
  3. extractionextracted with methylene chloride
  4. dry with materialthe extract is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residual oil is purified on a 200 g silica gel column with methylene chloride/ethyl acetate (10:1)
  8. customcrystallised from ether

Sources & evidence

ORD record
ord-1127c338a26d4f70aeacebf4f649fb3f
Source dataset
uspto-grants-1981_10
Patent number
US04294758

Reaction notes

Loading…