Sulfuric Acid → HCID 15279828, compound

HRID 2292869Notes

Reaction equation

HRID 2292869 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-2b1ee59d2b1643fb877883e9cdf32b13
Source dataset
uspto-grants-1997_11
Patent number
US05684196

Reaction notes

Loading…