Chlorine → HCID 86741706, compound

HRID 1788846Notes

Reaction equation

HRID 1788846 reaction equation
C(S[CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[CH:36]=[CH:35][C:34]([F: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:36]=[CH:35][C:34]([F: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

Participants

5

Reactant 2

HCID 24526ChlorineHCID 86741705HCID 86741705, compound

Product 1

HCID 86741706HCID 86741706, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.2 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(4-fluorophenoxy)-3-trimethylacetylthio-propenate (prepared as described in Example 25) in dichloromethane at -20°, was added a solution of 25 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 4.6 g of the title compound as a pale yellow foam (67% 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-e9f382e08b304749b5efb94d5aeae9b9
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

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