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

HRID 1448670Notes

Reaction equation

HRID 1448670 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) was 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 methylcyclohexane 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 methylcyclohexane

Sources & evidence

ORD record
ord-959744571a204f9b950211c5c6fc4668
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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