Water → HCID 19088750, compound

HRID 1463843Notes

Reaction equation

HRID 1463843 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[S-:11][C:12]#[N:13].[NH4+].[NH2:15][C:16]1[S:17][CH:18]=[C:19]([C:21]2[CH:30]=[CH:29][C:28]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=3[CH:22]=2)[N:20]=1.O>CC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:13][C:12]([NH:15][C:16]2[S:17][CH:18]=[C:19]([C:21]3[CH:30]=[CH:29][C:28]4[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=4[CH:22]=3)[N:20]=2)=[S:11])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 85014-Chlorobenzoyl chlorideHCID 15666Ammonium thiocyanateHCID 7350914-(5,6,7,8-Tetrahydronaphthalen-2-yl)-1,3-thiazol-2-amine

Product 1

HCID 19088750HCID 19088750, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

4-Chlorobenzoyl chloride (911 mg) was added to a solution of ammonium thiocyanate (460 mg) in acetone (20 ml), and the solution mixture was heated over a water bath for 1 minute and stirred at room temperature for 1 hour. A solution of 2-amino-4-(5,6,7,8-tetrahydro-2-naphthyl)thiazole (1.0 g) in acetone (10 ml) was added to the solution, followed by stirring at room temperature for 16 hours. The reaction mixture was poured into water, and the crystals which separated out were recovered by filtration and washed with water and hexane, successively. Recrystallization from dichloromethane-ethanol produced 1-(4-chlorobenzoyl)-3-[4-(5,6,7,8-tetrahydro-2-naphthyl-)2-thiazolyl]thiourea (Yield of 1.08 g, 58.1%) %) in the form of colorless needles. m.p. 193° to 194° C.

Workup

  1. temperaturethe solution mixture was heated over a water bath for 1 minute
  2. stirringby stirring at room temperature for 16 hours
  3. customthe crystals which separated out
  4. filtrationwere recovered by filtration
  5. washwashed with water and hexane
  6. customRecrystallization from dichloromethane-ethanol

Sources & evidence

ORD record
ord-27e5b20268c8499987e7eef6e059e188
Source dataset
uspto-grants-1994_04
Patent number
US05302608

Reaction notes

Loading…