Chlorine → HCID 86741707, compound

HRID 1788847Notes

Reaction equation

HRID 1788847 reaction equation
C(S[CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[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:38])[CH2:6]1)C=C.[Cl:39]Cl>ClCCl.C(Cl)(Cl)(Cl)Cl>[Cl:39][CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[C:24](=[O:29])[C:25]([CH3:27])([CH3:28])[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:38])[CH2:6]1

Participants

5

Reactant 2

HCID 24526ChlorineHCID 86741708HCID 86741708, compound

Product 1

HCID 86741707HCID 86741707, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.5 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-chlorophenoxy)-3-trimethylacetylthio-propenate in dichloromethane at -20° C. was added a solution of 1.7 mmol 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 0.3 g of the title compound as a pale yellow foam (65% 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-bee91b55d88744178ee3531d3b46f27f
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

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