N-bromobutanimide → HCID 70463777, compound

HRID 1902927Notes

Reaction equation

HRID 1902927 reaction equation
[CH3:1][C:2]1[CH2:3][S:4](=[O:24])[C@@H:5]2[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].[CH3:25][Si:26]([CH3:40])([CH3:39])NC(=O)C1C=CC([N+]([O-])=O)=CC=1.[Br:41]N1C(=O)CCC1=O>ClCCl>[Br:41][CH2:1][C:2]1[CH2:3][S:4](=[O:24])[C@@H:5]2[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([O:10][Si:26]([CH3:40])([CH3:39])[CH3:25])=[O:9]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 12726300N-trimethylsilyl-4-nitrobenzamideHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

263.4 mg of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide (0.76 mmoles) were added to a solution of 256 mg (1.08 mmoles) of N-trimethylsilyl-4-nitrobenzamide in 50 ml of dichloromethane and the clear solution that was obtained after refluxing this mixture for one hour was cooled in an ice-bath. Bromination was carried out in half an hour using 194.4 mg (1.09 mmoles) of N-bromosuccinimide as the brominating agent and some precipitate was formed after 20 minutes irradiation to obtain a 44% yield of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. customthe clear solution that was obtained
  2. temperatureafter refluxing this mixture for one hour
  3. temperaturewas cooled in an ice-bath
  4. waitBromination was carried out in half an hour
  5. customsome precipitate was formed after 20 minutes
  6. customirradiation

Sources & evidence

ORD record
ord-4432a1d16dba4119bb2eadc79bc32668
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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