Sulfuric Acid → 4-[3-(Trifluoromethyl)phenyl]-2,3-dihydro-1,3-thiazol-2-one

HRID 1667670Notes

Reaction equation

HRID 1667670 reaction equation
[S:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[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:9]1[CH:8]=[C:7]([C:5]2[NH:3][C:2](=[O:18])[S:1][CH:4]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 862452532-Oxo-2-[3-(trifluoromethyl)phenyl]ethyl thiocyanate

Product 1

HCID 432867304-[3-(Trifluoromethyl)phenyl]-2,3-dihydro-1,3-thiazol-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 26.42 g (107.74 mmole) of 2-thiocyanato-1-(3-trifluoromethyl-phenyl)-ethanone, 11 mL of 50% aqueous sulfuric acid and 55 mL of acetic acid was heated at reflux for 1 hour. The mixture was cooled, poured into 500 mL of ice water mixture and stirred for 30 minutes. The solid was collected by filtration, washing with water to give 24 g of 4-(3-trifluoromethyl-phenyl)-3H-thiazol-2-one as a light orange-brown solid.

Workup

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

Sources & evidence

ORD record
ord-ff5bfb7a1c7045aabaef34e02c926a8d
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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