Toluene → HCID 18964138, compound

HRID 261315Notes

Reaction equation

HRID 261315 reaction equation
C1(C)C=CC=CC=1.N1C=C[C:9]=1[C:12]([NH:14][CH:15]1[C:37](=[O:38])[N:17]2[CH:18]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[O:25])[C:19]([CH3:23])([CH3:22])[S:20](=[O:21])[C@H:16]12)=[O:13].[Cl:39]N1C(=O)CCC1=O>O>[CH3:22][C:19](=[CH2:23])[CH:18]([N:17]1[C:37](=[O:38])[CH:15]([NH:14][C:12](=[O:13])[CH3:9])[CH:16]1[S:20]([Cl:39])=[O:21])[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:25]

Participants

5

Reactant 3

HCID 1140TolueneHCID 31398ChlorosuccinimideHCID 70610690HCID 70610690, compound

Product 1

HCID 18964138HCID 18964138, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Toluene (500 ml.) was heated in equipment containing a Dean-Stark water trap to azeotropically remove any moisture which may be present. To the resulting dried toluene was added 1.0 gms. (2.4 mmol.) of p-nitrobenzyl 6-azetamido-2,2-dimethylpenam-3-carboxylate-1-oxide. The resulting mixture was refluxed again using a Dean-Stark water trap to remove any additional amounts of water which may be present. The mixture then was cooled, and 400 mg. (2.9 mmol) of N-chlorosuccinimide were added. The mixture then was refluxed for 1 hour. A sample of the reaction mixture was withdrawn, and the solvent was removed. The product which was obtain was consistent by nmr analysis with the structure of the title compound.

Workup

  1. customto azeotropically remove any moisture which
  2. additionTo the resulting dried toluene was added 1.0 gms
  3. temperatureThe resulting mixture was refluxed again
  4. customto remove any additional amounts of water which
  5. temperatureThe mixture then was cooled
  6. temperatureThe mixture then was refluxed for 1 hour
  7. customA sample of the reaction mixture was withdrawn
  8. customthe solvent was removed
  9. customThe product which was obtain

Sources & evidence

ORD record
ord-9ed814a8d3634a7a8ce18dcf27f42447
Source dataset
uspto-grants-1979_08
Patent number
US04165315

Reaction notes

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