Thionyl Chloride → HCID 12833906, compound

HRID 2058993Notes

Reaction equation

HRID 2058993 reaction equation
[F:1][C:2]([F:18])([F:17])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14](O)=[O:15])(=[O:5])=[O:4].S(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[F:1][C:2]([F:18])([F:17])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([Cl:21])=[O:15])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12833905HCID 12833905, compound

Product 1

HCID 12833906HCID 12833906, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 10 g of o-(trifluoromethanesulfonamido)phenylacetic acid in 100 ml of chloroform, there were dropwise added 8.4 g of thionyl chloride. After completion of the addition, the resultant mixture was heated and refluxed until the evolution of the gas stopped. Concentration of the reaction mixture gave a solid substance, which was recrystallized from toluene to give 7.6 g of o-(trifluoromethanesulfonamido)phenylacetyl chloride. M.P. 94°-95° C.

Workup

  1. additionAfter completion of the addition
  2. temperaturerefluxed until the evolution of the gas
  3. customConcentration of the reaction mixture gave a solid substance, which
  4. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-135f272e0c444523a147c680884b5e8a
Source dataset
uspto-grants-1982_03
Patent number
US04321081

Reaction notes

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