Carbon Tetrachloride → 3-bromo-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H, 5H)-dione

HRID 704556Notes

Reaction equation

HRID 704556 reaction equation
[Br:1]Br.C(Cl)(Cl)(Cl)Cl.[CH3:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12](=[O:26])[CH2:11][C:10]1=[O:27]>C(Cl)Cl>[Br:1][CH:11]1[C:10](=[O:27])[N:9]([CH3:8])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:12]1=[O:26]

Participants

5

Reactant 3

HCID 5943Carbon Tetrachloride2×HCID 24408BromineHCID 146976571-Methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 146976583-bromo-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4-(3H, 5H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While irradiating with a 500 watt lamp at about 40° C., a solution of 5 ml of bromine and 30 ml of carbon tetrachloride was introduced dropwise into a solution of 25 g of the product of Step A and 750 ml of carbon tetrachloride. At the end of the introduction, the lamp was extinguished, the mixture was cooled and 500 ml of methylene chloride were added. The organic phase was washed with a saturated sodium carbonate solution, then with water and the product obtained was chromatographed on silica. Elution with an ethyl acetate-methylene chloride mixture 7-3-yielded 10.5 g of the sought product melting at 132° C.

Workup

  1. customWhile irradiating with a 500 watt lamp at about 40° C.
  2. temperaturethe mixture was cooled
  3. washThe organic phase was washed with a saturated sodium carbonate solution
  4. customwith water and the product obtained
  5. customwas chromatographed on silica
  6. washElution with an ethyl acetate-methylene chloride mixture 7-3-yielded 10.5 g of the sought product melting at 132° C.

Sources & evidence

ORD record
ord-7b5917404f58451d91da8598e69df656
Source dataset
uspto-grants-1991_01
Patent number
US04988692

Reaction notes

Loading…