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

HRID 443699Notes

Reaction equation

HRID 443699 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-0cc711386de64531a8cffa66b4c75a1b
Source dataset
uspto-grants-1981_04
Patent number
US04261728

Reaction notes

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