Toluene → HCID 18964138, compound

HRID 1679573Notes

Reaction equation

HRID 1679573 reaction equation
C1(C)C=CC=CC=1.[C:8]([NH:11][CH:12]1[C:34](=[O:35])[N:14]2[CH:15]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[C:16]([CH3:20])([CH3:19])[S:17](=[O:18])[C@H:13]12)(=[O:10])[CH3:9].[Cl:36]N1C(=O)CCC1=O>O>[CH3:19][C:16](=[CH2:20])[CH:15]([N:14]1[C:34](=[O:35])[CH:12]([NH:11][C:8](=[O:10])[CH3:9])[CH:13]1[S:17]([Cl:36])=[O:18])[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:22]

Participants

5

Reactant 3

HCID 1140TolueneHCID 31398ChlorosuccinimideHCID 70621571HCID 70621571, 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-acetamido-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 A sample of the reaction mixture was withdrawn, and the solvent was removed.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 customA sample of the reaction mixture was withdrawn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-8e90a27059c34936afabca2c2fafd4b1
Source dataset
uspto-grants-1978_03
Patent number
US04081440

Reaction notes

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