Sulfuric Acid → 4-(4-Chlorophenyl)-1,3-thiazol-2(3H)-one

HRID 1830865Notes

Reaction equation

HRID 1830865 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([S:11][C:12]#[N:13])=O)=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:15]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:15])[S:11][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22049674HCID 22049674, compound

Product 1

HCID 2446344-(4-Chlorophenyl)-1,3-thiazol-2(3H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound (40)(10.9 mg, 52.2 mmol) was suspended in acetic acid (50 ml) and 50% sulfuric acid (15 ml) was added dropwise at 60° C. The mixture was heated under reflux for 2 hrs. After cooling, the reaction mixture added to ice (200 g). The precipitated crystals were collected by filtration, washed twice with water (200 ml) and dried under reduced pressure to give the title compound (10.1 g, 91%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. temperatureAfter cooling
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed twice with water (200 ml)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-7881fce6ce32473387fbb062a3eb449c
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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