Thionyl Chloride → p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-chloroacetate

HRID 1680323Notes

Reaction equation

HRID 1680323 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].S(Cl)([Cl:27])=O>ClCCl>[C:1]([S:4][CH:5]1[N:8]([CH:9]([Cl:27])[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 24386Thionyl ChlorideHCID 13132061HCID 13132061, compound

Product 1

HCID 13132062p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-chloroacetateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of acid 1 (19.36 g), thionyl chloride (40 ml) and dichloromethane (200 ml) was stirred at 23° for 18 h. The solvent and excess thionyl chloride were evaporated in vacuo at 23° to give acid chloride 2 as an off-white solid, 20.5 g (99% yield). ##STR123##

Workup

  1. customThe solvent and excess thionyl chloride were evaporated in vacuo at 23°

Sources & evidence

ORD record
ord-ffa8268d9854461896c907dc44f8e3ac
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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