Chlorosuccinimide → HCID 20394786, compound

HRID 1679564Notes

Reaction equation

HRID 1679564 reaction equation
[C:1]1(=[O:35])[N:5]([C@@H:6]2[C:28](=[O:29])[N:8]3[CH:9]([C:15]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=4)=[O:16])[C:10]([CH3:14])([CH3:13])[S:11](=[O:12])[C@H:7]23)[C:4](=[O:30])[C:3]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:2]12.[Cl:36]N1C(=O)CCC1=O>ClCCCl>[CH3:13][C:10](=[CH2:14])[CH:9]([N:8]1[C:28](=[O:29])[CH:6]([N:5]2[C:4](=[O:30])[C:3]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:2]3[C:1]2=[O:35])[CH:7]1[S:11]([Cl:36])=[O:12])[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 70610277HCID 70610277, compound

Product 1

HCID 20394786HCID 20394786, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 49.7 g. (0.1 mol) p-nitrobenzyl 6β-phthalimido-2,2-dimethylpenam-3-carboxylate-1-oxide and 13.4 g. (0.1 mol.) of N-chlorosuccinimide in 1.5 L. of 1,2-dichloroethane was refluxed for 70 minutes. The mixture was cooled, washed with water and brine, and then dried over MgSO4. The solvent then was evaporated, and the residue was dried in vacuo for 3 hours to obtain 52.0 g. of the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent then was evaporated
  5. customthe residue was dried in vacuo for 3 hours
  6. customto obtain 52.0 g

Sources & evidence

ORD record
ord-94c64ae8f3ab42daad3b9cb94d3a2cab
Source dataset
uspto-grants-1978_03
Patent number
US04081440

Reaction notes

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