Benzenesulfonyl fluoride, 3-(bromoacetyl)- → HCID 20461261, compound

HRID 434324Notes

Reaction equation

HRID 434324 reaction equation
C(N(CC)[CH:4]=[C:5]([C:11](=[S:21])[NH:12][C:13]([O:15][CH2:16][C:17]([Cl:20])([Cl:19])[Cl:18])=[O:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[F:24][S:25]([C:28]1[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=1)[C:31](=[O:34])[CH2:32]Br)(=[O:27])=[O:26]>C(O)(C)C>[F:24][S:25]([C:28]1[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=1)[C:31]([C:32]1[S:21][C:11]([NH:12][C:13]([O:15][CH2:16][C:17]([Cl:18])([Cl:19])[Cl:20])=[O:14])=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=1)=[O:34])(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 5066471Benzenesulfonyl fluoride, 3-(bromoacetyl)-HCID 54431333HCID 54431333, compound

Product 1

HCID 20461261HCID 20461261, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 25 g (0.061 m) of ethyl 3-diethylamino-2-[N-(2,2,2-trichloroethoxycarbonyl)thiocarbamoyl]acrylate, 17.15 g (0.061 m) of m-fluorosulfonylphenacyl bromide, and 125 ml of isopropyl alcohol was heated to reflux for 5 minutes. The reactants dissolved at reflux, and shortly thereafter the product precipitated. The mixture was cooled and the solid collected by filtration. The solid was washed with isopropyl alcohol and then water to give 27.6 g (85 percent) of product, melting point 108° to 110° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 minutes
  3. dissolutionThe reactants dissolved
  4. temperatureat reflux
  5. customshortly thereafter the product precipitated
  6. temperatureThe mixture was cooled
  7. filtrationthe solid collected by filtration
  8. washThe solid was washed with isopropyl alcohol

Sources & evidence

ORD record
ord-d7f46de5e1ac48b4bfec77fe781d52e5
Source dataset
uspto-grants-1983_08
Patent number
US04396546

Reaction notes

Loading…