Sulfuric Acid → 4-(4-trifluoromethyl-phenyl)-3H-thiazol-2-one

HRID 1667662Notes

Reaction equation

HRID 1667662 reaction equation
[S:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O)[C:2]#[N:3].S(=O)(=O)(O)[OH:18]>C(O)(=O)C>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([C:5]2[NH:3][C:2](=[O:18])[S:1][CH:4]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 575420642-Thiocyanato-1-(4-trifluoromethyl-phenyl)-ethanone

Product 1

HCID 432868074-(4-trifluoromethyl-phenyl)-3H-thiazol-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 22.52 g (91.8 mmole) of 2-thiocyanato-1-(4-trifluoromethyl-phenyl)-ethanone 9 mL of 50% aqueous sulfuric acid and 45 mL of acetic acid was heated at reflux for 1.5 hours. The mixture was cooled, poured into 500 mL of ice water and stirred for 30 minutes. The solid was collected by filtration, washing with water, to give 21.33 g of 4-(4-trifluoromethyl-phenyl)-3H-thiazol-2-one as a tan solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe mixture was cooled
  4. filtrationThe solid was collected by filtration
  5. washwashing with water

Sources & evidence

ORD record
ord-73bbd9e4e1594d838e98bb1826b0a963
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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