Water → 5-(2-(Benzyloxy)-4-chlorophenyl)-1,3,4-oxathiazol-2-one

HRID 453118Notes

Reaction equation

HRID 453118 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:20]([S:22]Cl)=[O:21].O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[C:11]1[O:12][C:20](=[O:21])[S:22][N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 75990(Chlorothio)formyl chlorideHCID 47467978HCID 47467978, compound

Product 1

HCID 595495295-(2-(Benzyloxy)-4-chlorophenyl)-1,3,4-oxathiazol-2-oneYield 98.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(benzyloxy)-4-chlorobenzamide (0.103 g, 0.38 mmol) in toluene (5 ml) was added chlorocarbonylsulfenyl chloride (63 μL, 0.76 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 (3×25 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 (0.12 g, 94%) that was carried forward as such without further purification. MS: 320.21 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. additionwas added
  3. extractionfollowed by extraction with ether (3×25 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-7cfbe8c12776402c8e8bea53b24b7eb0
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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