Water → 5-(4-Chloro-2-methoxyphenyl)-1,3,4-oxathiazol-2-one

HRID 453111Notes

Reaction equation

HRID 453111 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.Cl[C:14]([S:16]Cl)=[O:15].O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][C:14](=[O:15])[S:16][N:8]=2)=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 75990(Chlorothio)formyl chlorideHCID 19741766HCID 19741766, compound

Product 1

HCID 595495245-(4-Chloro-2-methoxyphenyl)-1,3,4-oxathiazol-2-oneYield 95.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-2-methoxybenzamide (0.82 g, 4.42 mmol) in toluene (20 ml) was added chlorocarbonylsulfenyl chloride (0.73 ml, 8.84 mmol) under nitrogen atmosphere and the resulting reaction mixture was refluxed at 90° C. for 2 h. After the completion of the reaction (TLC monitoring) water was added followed by extraction with ether (3×50 ml). The combined organics was then sequentially washed with water, 10% NaHCO3 (aqueous solution) and finally again with water. The organic layer was then dried over anhydrous Na2SO4, filtered and concentrated to get desired product (1.03 g, 96% crude yield) that was carried forward as such without further purification. MS: 244.16 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. additionwas added
  3. extractionfollowed by extraction with ether (3×50 ml)
  4. washThe combined organics was then sequentially washed with water, 10% NaHCO3 (aqueous solution) and finally again with water
  5. dry with materialThe organic layer was then dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-67797e54e86642398735e9dd5561b00f
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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