Benzamide → 5-phenyl-1,3,4-oxathiazol-2-one

HRID 1847255Notes

Reaction equation

HRID 1847255 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:11]([S:13]Cl)=[O:12]>C1(C)C=CC=CC=1>[C:2]1([C:1]2[O:8][C:11](=[O:12])[S:13][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2331BenzamideHCID 75990(Chlorothio)formyl chloride

Product 1

HCID 8531705-phenyl-1,3,4-oxathiazol-2-oneYield 79.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of benzamide (66.03 mmol) in toluene (132 mL) was added chlorocarbonylsulfenyl chloride (82.4 mmol). The reaction mixture was stirred at 100° C. for 4 h. After cooling to r.t. the reaction mixture was concentrated in vacuo, and the residue was crystallized from EtOAc to give the title compound (9.43 g) as a white solid: MS (m/z) 179.1 (M+1).

Workup

  1. temperatureAfter cooling to r.t. the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customthe residue was crystallized from EtOAc

Sources & evidence

ORD record
ord-7cf28d4e62c342b1aa91a74421b3a7ab
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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