Chlorine → HCID 86741709, compound

HRID 1788850Notes

Reaction equation

HRID 1788850 reaction equation
C(S[CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[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:41])[CH2:6]1)C=C.[Cl:42]Cl>ClCCl.C(Cl)(Cl)(Cl)Cl>[Cl:42][CH:5]1[N:8]([C:9](=[C:23]([O:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[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:41])[CH2:6]1

Participants

5

Reactant 2

HCID 24526ChlorineHCID 86741710HCID 86741710, compound

Product 1

HCID 86741709HCID 86741709, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.1 g of 4-nitrobenzyl 2-(4-allylthioazetidin-2-on-1-yl)-3-(1-naphthyloxy)-3-trimethylacetylthiopropenate in dichloromethane at -20° was added a solution of 23 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 4.898 g of the title compound as a pale yellow foam (75% 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-a21876ed30be4c5880830910e25f5acc
Source dataset
uspto-grants-1987_08
Patent number
US04684640

Reaction notes

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