Water → 4-phenyl-N-propyl-1,3-thiazol-2-amine

HRID 2422236Notes

Reaction equation

HRID 2422236 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH2:11]([NH:14][C:15]([NH2:17])=[S:16])[CH2:12][CH3:13].C([O-])(=O)C.[Na+].O>C(O)C>[C:5]1([C:3]2[N:17]=[C:15]([NH:14][CH2:11][CH2:12][CH3:13])[S:16][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 107572-ChloroacetophenoneHCID 517045Sodium AcetateHCID 1615208Propyl-2-thiourea

Product 1

HCID 230827804-phenyl-N-propyl-1,3-thiazol-2-amineYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloroacetophenone (4.45 g, 28.8 mmol) and N-propylthiourea (3.40 g, 28.8 mmol) in ethanol (50 mL) was added sodium acetate (3.07 g, 37.4 mmol), and the mixture was heated under reflux for 1.5 hrs. Water was added to the reaction mixture, and crystals were collected by filtration. The obtained crude crystals were recrystallized from diethyl ether-hexane to give the title compound (5.64 g, 92%) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hrs
  3. filtrationwere collected by filtration
  4. customThe obtained crude crystals
  5. customwere recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-1309f79e1cdd4cc4ba387db37e1eb03d
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

Loading…