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

HRID 1679568Notes

Reaction equation

HRID 1679568 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-29f56c30db204ce89d77a4040920ebfb
Source dataset
uspto-grants-1978_03
Patent number
US04081440

Reaction notes

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