Oxalyl chloride → p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-chloroacetate

HRID 355218Notes

Reaction equation

HRID 355218 reaction equation
[C:1]([S:4][CH:5]1[N:8]([CH:9](O)[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:24])[CH2:6]1)(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:28])=O>CN(C)C=O>[C:1]([S:4][CH:5]1[N:8]([CH:9]([Cl:28])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 13132061HCID 13132061, compound

Product 1

HCID 13132062p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-chloroacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a mixture of acid 1 (10.0 g, 79 mmoles) in 100 ml of oxalyl chloride was added one drop of dimethylformamide. The mixture was stirred for 1.15 h at 23° and then the excess oxalyl chloride was distilled off at 23° and 10-20 torr to give acid chloride 2 as a brown oil, 11.4 (100%). ##STR182##

Workup

  1. distillationthe excess oxalyl chloride was distilled off at 23°

Sources & evidence

ORD record
ord-a9df11ffe0aa4682a255e558c4b75e2f
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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