N-chloro-N-methyl-p-toluenesulfonamide → Methyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate

HRID 261311Notes

Reaction equation

HRID 261311 reaction equation
[C:1]1(=[O:26])[N:5]([CH: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]N(C)S(C1C=CC(C)=CC=1)(=O)=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 13017215N-chloro-N-methyl-p-toluenesulfonamideHCID 70610153Methyl 6-phthalimido-2,2-dimethylpenam-3-carboxylate-1-oxide

Product 1

HCID 20394803Methyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 300 ml of carbon tetrachloride were added 3.7 g. (10 mmole) of methyl 6-phthalimido-2,2-dimethylpenam-3-carboxylate-1-oxide and 2.2 g. (10 mmol.) of N-chloro-N-methyl-p-toluenesulfonamide. The mixture was heated at reflux for 90 minutes. The reaction mixture then was cooled to room temperature, washed with water and brine, dried over magnesium sulfate, and divided into two equal portions.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 minutes
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-ab9a9c609740483d8cd680f746de75e8
Source dataset
uspto-grants-1979_08
Patent number
US04165315

Reaction notes

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