(Chlorothio)formyl chloride → 5-(4-Benzyloxyphenyl)-[1,3,4]oxathiazol-2-one

HRID 72315

Reaction equation

HRID 72315 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19]([S:21]Cl)=[O:20]>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[O:14][C:19](=[O:20])[S:21][N:15]=2)=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 27264314-Benzyloxybenzamide

Product 1

HCID 595495255-(4-Benzyloxyphenyl)-[1,3,4]oxathiazol-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

4-benzyloxybenzamide (0.66 g, 2.98 mmol) and 0.26 ml of chlorocarbonyl sulfenyl chloride were dissolved in 10 ml of benzene, refluxed for 3 hours, and stirred at 50° C. for 12 hours. The organic solvent was distilled off under reduced pressure, and the resulting solid was washed with n-hexane to obtain 0.78 g of 5-(4-benzyloxy-phenyl)-[1,3,4]oxathiazol-2-one.

Workup

  1. temperaturerefluxed for 3 hours
  2. distillationThe organic solvent was distilled off under reduced pressure
  3. washthe resulting solid was washed with n-hexane

Sources & evidence

ORD record
ord-fbc85fb8b0574939b8b9d725112b0166
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Linked notes

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