Sodium Carbonate → HCID 20562335, compound

HRID 848136Notes

Reaction equation

HRID 848136 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[Cl:22])[C:6]=2[CH:23]=1.[Br:24]Br.C(=O)([O-])[O-].[Na+].[Na+]>Br>[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[Cl:22])[C:6]=2[C:23]=1[Br:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 20562367HCID 20562367, compound

Product 1

HCID 20562335HCID 20562335, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
0 °C

Procedure

9.6 g (0.029 M) of rac-7-amino-3-ethyl-5-(o-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one dissolved in 50 ml of concentrated aqueous hydrobromic acid are treated slowly at between 0°-5° C. with 5.2 g (1.65 ml) of bromine and the mixture is stirred at 0° C. for 1 hour. The mixture is then poured on to a mixture of ice and sodium carbonate solution, extracted with methylene chloride and the extract is dried over sodium sulphate, filtered and concentrated. After crystallisation from methylene chloride/ether/petroleum ether, there is obtained rac-7-amino-3-ethyl-6-bromo-5-(o-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one which melts at 251° C. with decomposition.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialthe extract is dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customAfter crystallisation from methylene chloride/ether/petroleum ether

Sources & evidence

ORD record
ord-eea7e4bc24d84cbab49814acc61d9960
Source dataset
uspto-grants-1981_10
Patent number
US04294758

Reaction notes

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