Chlorosuccinimide → Methyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate

HRID 261306Notes

Reaction equation

HRID 261306 reaction equation
[C:1]1(=[O:26])[N:5]([C@@H:6]2[C:19](=[O:20])[N:8]3[CH:9]([C:15]([O:17][CH3:18])=[O:16])[C:10]([CH3:14])([CH3:13])[S:11](=[O:12])[C@H:7]23)[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12.[Cl:27]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:13][C:10](=[CH2:14])[CH:9]([N:8]1[C:19](=[O:20])[CH:6]([N:5]2[C:4](=[O:21])[C:3]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]3[C:1]2=[O:26])[CH:7]1[S:11]([Cl:27])=[O:12])[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 70611337Methyl 6beta-phthalimido-2,2-dimethylpenam-3-carboxylate-1-oxide

Product 1

HCID 20394803Methyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoateYield 95%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 18.8 g. (50 mmol) of methyl 6β-phthalimido-2,2-dimethylpenam-3-carboxylate-1-oxide and 6.7 g. (50 mmol) of N-chlorosuccinimide in 1000 ml. of dry carbon tetrachloride was refluxed for 70 minutes. The mixture was cooled and then was washed with water and brine. After drying over MgSO4, the solvent was evaporated, and 19.5 g. (95%) of the title compound as a colorless solid was obtained. The nmr spectrum (CDCl3) indicates that the product is the sulfinyl chloride.

Workup

  1. temperatureThe mixture was cooled
  2. washwas washed with water and brine
  3. dry with materialAfter drying over MgSO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-03d3bedcca31443aa63d0840b620d38c
Source dataset
uspto-grants-1979_08
Patent number
US04165315

Reaction notes

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