p-METHYLACETOPHENONE → 4-(4-Methylphenyl)-1,3-thiazol-2(3H)-imine

HRID 1708944Notes

Reaction equation

HRID 1708944 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH3:13])=[CH:8][CH:7]=1.S(Cl)(Cl)(=O)=O>CC(C)=O>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:1]=[C:2]([NH2:4])[S:3][CH:13]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8500p-METHYLACETOPHENONEHCID 24648Sulfuryl chlorideHCID 2723790Thiourea

Product 1

HCID 2440664-(4-Methylphenyl)-1,3-thiazol-2(3H)-imineYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of thiourea (2.18 g, 28.6 mmol) and p-methylacetophenone (1.92 ml, 14.3 mmol) was added dropwise sulfuryl chloride (1.264 ml, 15.74 mmol) and the resulting mixture was stirred at room temperature for 10 minutes (until solidification was complete). The reaction mixture was allowed to react at 105° C. for 3 hours and acetone was added thereto. Then insoluble matters were filtered with suction, treated with 300 ml of water and heated at 80° C. Insoluble solids were removed by filtration. After the filtrate was made alkaline (pH 11) with 1N-KOH under ice-cooling, the deposited solids were filtered with suction, washed with water and recrystallized from methanol-water to afford 1.46 g (yield 54%) of 4-(4-methylphenyl)-2-thiazolamine as pale yellowish crystals, m.p.130° C.

Workup

  1. customto react at 105° C. for 3 hours
  2. filtrationThen insoluble matters were filtered with suction
  3. additiontreated with 300 ml of water
  4. temperatureheated at 80° C
  5. customInsoluble solids were removed by filtration
  6. temperaturecooling
  7. filtrationthe deposited solids were filtered with suction
  8. washwashed with water
  9. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-8b66f114502f4c2f9cac5cb7a3d149f4
Source dataset
uspto-grants-1990_08
Patent number
US04946855

Reaction notes

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