Benzene → HCID 131711474, compound

HRID 26042Notes

Reaction equation

HRID 26042 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:44](=[O:45])[N:14]2[C:15]([C:28]([O:30][CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])=[C:16]([CH:20]=[CH:21][C:22]3[N:26]([CH3:27])[N:25]=[N:24][N:23]=3)[CH2:17][S:18](=O)[C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[K+].C(Cl)(=O)C.C1C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:44](=[O:45])[N:14]2[C:15]([C:28]([O:30][CH:31]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:29])=[C:16]([CH:20]=[CH:21][C:22]3[N:26]([CH3:27])[N:25]=[N:24][N:23]=3)[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 4875Potassium IodideHCID 6367Acetyl chlorideHCID 131711473benzhydryl 7-phenoxyacetamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 131711474HCID 131711474, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1.3 g of benzhydryl 7-phenoxyacetamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate-1-oxide in 25 ml of N,N-dimethylformamide were added with stirring under cooling with a freezing mixture 2.0 g of potassium iodide and 0.7 ml of acetyl chloride, and the mixture was stirred for 5 minutes. The mixture was then stirred for another 90 minutes at room temperature and poured into ice-water. The separating oil was extracted with ethyl acetate. The extract was washed with an aqueous potassium metabisulfite solution, water, a dilute aqueous sodium hydrogencarbonate solution and water successively and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to leave a residue. The obtained residue was developed through silica gel column with a mixture of benzene and ethyl acetate (1:1) to give 1.1 g of benzhydryl 7-phenoxyacetamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylate.

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. stirringThe mixture was then stirred for another 90 minutes at room temperature
  3. extractionThe separating oil was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous potassium metabisulfite solution, water
  5. dry with materiala dilute aqueous sodium hydrogencarbonate solution and water successively and dried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto leave a residue

Sources & evidence

ORD record
ord-d1ad34af233240ffb5054f2b6b4a8784
Source dataset
uspto-grants-1979_04
Patent number
US04147863

Reaction notes

Loading…