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

HRID 261313Notes

Reaction equation

HRID 261313 reaction equation
[O:1]([CH2:8][C:9]([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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:36]N(C)S(C1C=CC(C)=CC=1)(=O)=O>>[CH3:19][C:16](=[CH2:20])[CH:15]([N:14]1[C:34](=[O:35])[CH:12]([NH:11][C:9](=[O:10])[CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[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

3

Reactant 2

HCID 13017215N-chloro-N-methyl-p-toluenesulfonamideHCID 67928276p-Nitrobenzyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide

Product 1

HCID 9936995p-Nitrobenzyl 3-Methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate

Procedure

To 150 ml. of distilled and molecular sieve-dried toluene were added 3.0 g. (6 mmol.) of p-nitrobenzyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide and 1.3 g. (6 mmol.) of N-chloro-N-methyl-p-toluenesulfonamide. The mixture was heated at reflux for 60 minutes. The resulting reaction mixture then was cooled to room temperature. An aliquot (15 ml.) was separated, washed with water, and brine, dried over magnesium sulfate, and evaporated to dryness in vacuo. The nmr spectrum of the residue was consistent for the title compound contaminated with some N-methyl-p-toluenesulfonamide.

Workup

  1. distillationof distilled
  2. additionmolecular sieve-dried toluene were added 3.0 g
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 60 minutes
  5. customThe resulting reaction mixture
  6. customAn aliquot (15 ml.) was separated
  7. washwashed with water, and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a641228144254f99a5c289426dabe60c
Source dataset
uspto-grants-1979_08
Patent number
US04165315

Reaction notes

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