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

HRID 1963010Notes

Reaction equation

HRID 1963010 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Cl[C:12]([S:14]Cl)=[O:13]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][C:12](=[O:13])[S:14][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 120844-ChlorobenzamideHCID 75990(Chlorothio)formyl chloride

Product 1

HCID 8194535-(4-chlorophenyl)-1,3,4-oxathiazol-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chlorobenzamide (1.0 g, 6.42 mmol) in toluene (25 ml) was added chlorocarbonylsulfenyl chloride (1.0 ml, 12.85 mmol). The resulting reaction mixture was refluxed at 80° C. for 3 h. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added diethyl ether and washed twice with water, twice with 5% NaHCO3, again with water, and was dried (Na2SO4), concentrated under vacuum to give the product (crude yield 1.37 g, 100%) that was carried forward to the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. concentrationthe mixture was concentrated
  4. additionadded diethyl ether
  5. washwashed twice with water, twice with 5% NaHCO3, again with water
  6. dry with materialwas dried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customto give the product (crude yield 1.37 g, 100%) that
  9. customwas carried forward to the next step without further purification

Sources & evidence

ORD record
ord-d8fbdce758a14dc59101fae7679a5723
Source dataset
uspto-grants-2013_04
Patent number
US08415383B2

Reaction notes

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