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

HRID 443702Notes

Reaction equation

HRID 443702 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-32f566f8623f43a389b5f0484bb80896
Source dataset
uspto-grants-1981_04
Patent number
US04261728

Reaction notes

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