m-Toluamide → 5-(3-Methylphenyl)-2H-1,3,4-oxathiazol-2-one

HRID 614170Notes

Reaction equation

HRID 614170 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH2:9])=[O:8])[CH:2]=1.Cl[C:12]([S:14]Cl)=[O:13]>C1(C)C=CC=CC=1.CC1CCCCC1>[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:8][C:12](=[O:13])[S:14][N:9]=2)[CH:2]=1

Participants

5

Reactant 2

HCID 69253m-ToluamideHCID 75990(Chlorothio)formyl chloride

Product 1

HCID 124373965-(3-Methylphenyl)-2H-1,3,4-oxathiazol-2-oneYield 45.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7962MethylcyclohexaneSolvent

Procedure

m-Toluamide (116 g, 0.86 mol) and chlorocarbonylsulfenyl chloride (144 g, 1.1 mol, 28% excess) were heated to 100° C. in 400 ml of toluene, with stirring, for 5.5 hours. Cooling resulted in an orange solid. The solid, isolated by filtration, was dissolved in hot methylcyclohexane and decolorized. The light yellow product was recrystallized once from methyl-cyclohexane to give 76.05 g (45.8%) of white solid, m.p. 82. 5°-84°.

Workup

  1. temperatureCooling
  2. customresulted in an orange solid
  3. customThe solid, isolated by filtration
  4. customThe light yellow product was recrystallized once from methyl-cyclohexane

Sources & evidence

ORD record
ord-f6c977f7c4114d0ab64a590952b52a75
Source dataset
uspto-grants-1979_03
Patent number
US04144047

Reaction notes

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