Sulfuric Acid → HCID 15279828, compound

HRID 265728Notes

Reaction equation

HRID 265728 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:13][C:14](Cl)=[CH2:15])[C:10]([NH2:12])=[S:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>O>[NH:12]=[C:10]1[N:9]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=2)[CH:13]=[C:14]([CH3:15])[S:11]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 15279827HCID 15279827, compound

Product 1

HCID 15279828HCID 15279828, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

N-(3,5-dichlorophenyl)-N-(2-chloro-2-propenyl)thiourea (0.30 g) was added to 90% sulfuric acid (3.5 g) at room temperature with stirring, and the mixture was heated to 90° C. and stirred at the same temperature for 1.0 hour. After cooling, water was added to the reaction mixture, which was then neutralized by addition of sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water. The solvent was removed by distillation under reduced pressure, and the residual oily material was subjected to column chromatography on silica gel, which afforded 0.16 g of 2-imino-3-(3,5-dichlorophenyl)-5-methyl-4-thiazoline (62% yield).

Workup

  1. stirringstirred at the same temperature for 1.0 hour
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-ed76210c2e834a2bab341627ce845807
Source dataset
uspto-grants-1997_07
Patent number
US05648533

Reaction notes

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