Chlorine → HCID 86741713, compound

HRID 1788854Notes

Reaction equation

HRID 1788854 reaction equation
C(S[CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH3:39])=[O:38])=[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:40])[CH2:6]1)C=C.[Cl:41]Cl>ClCCl.C(Cl)(Cl)(Cl)Cl>[Cl:41][CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH3:39])=[O:38])=[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:40])[CH2:6]1

Participants

5

Reactant 2

HCID 24526ChlorineHCID 86741714HCID 86741714, compound

Product 1

HCID 86741713HCID 86741713, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.488 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-methylsulphinylphenoxy)-3-trimethylacetylthiopropenate in dichloromethane at -20°, was added dropwise a solution of 1.58 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 0.24 g of the title compound as a pale yellow foam (53% 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-7c95f89235eb4b3db8041d63efaff3e4
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

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