Chlorine → HCID 86740754, compound

HRID 1381209Notes

Reaction equation

HRID 1381209 reaction equation
C(S[CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[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)=[S:11])[C:7](=[O:37])[CH:6]1[CH2:38][CH3:39])C=C.[Cl:40]Cl>ClCCl.C(Cl)(Cl)(Cl)Cl>[Cl:40][CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[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)=[S:11])[C:7](=[O:37])[CH:6]1[CH2:38][CH3:39]

Participants

5

Reactant 2

HCID 24526ChlorineHCID 86740755HCID 86740755, compound

Product 1

HCID 86740754HCID 86740754, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.47 g 4-nitrobenzyl 2-(4-allylthio-3-ethylazetidin-2-on-1-yl)-3-phenoxy-3-trimethylacetylthiopropenate in dichloromethane at -20° was added a solution of 8.4 mmol of chlorine in carbon tetrachloride. After 30 minutes the mixture was warmed to room temperature, evaporated in vacuo, and the residual oil was chromatographed over silica gel. Elution with hexane - ethyl acetate mixtures afforded 1.782 g of the title compound as a pale yellow foam (78% of the theoretical yield).

Workup

  1. customevaporated in vacuo
  2. customthe residual oil was chromatographed over silica gel
  3. washElution with hexane - ethyl acetate mixtures

Sources & evidence

ORD record
ord-01d2b1d39ca14fa684a48902d8a1f5c4
Source dataset
uspto-grants-1986_04
Patent number
US04585767

Reaction notes

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