(Chlorothio)formyl chloride → 5-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-xylyl)-1,3,4-oxathiazol-2-one

HRID 614173Notes

Reaction equation

HRID 614173 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([NH2:8])=[O:7].Cl[C:19]([S:21]Cl)=[O:20]>C1(C)C=CC=CC=1.CCCCCC.CO>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[C:5]([C:6]2[O:7][C:19](=[O:20])[S:21][N:8]=2)[CH:9]=[C:10]([C:12]([F:15])([F:13])[F:14])[CH:11]=1

Participants

6

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 5199273,5-Bis(trifluoromethyl)benzamide

Product 1

HCID 124374035-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-xylyl)-1,3,4-oxathiazol-2-oneYield 29.75%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

3,5-Bis(trifluoromethyl)benzamide (60.5 g, 0.235 mol) and five equivalents of chlorocarbonylsulfenyl chloride (154 g, 1.175 mol) were heated in 600 ml of toluene at reflux, with stirring, for 12 hours. The crude product, a dark brown oil, weighed 77.5 g. After decolorization in hexane, the material was taken up in methanol and recrystallized three times to give 22.0 g (0.0699 mol, 29.75%) of pale gold solid, m.p. 61°-62.5°.

Workup

  1. temperatureat reflux
  2. customrecrystallized three times

Sources & evidence

ORD record
ord-0f996865842d41d1b6fc6797579548c7
Source dataset
uspto-grants-1979_03
Patent number
US04144047

Reaction notes

Loading…