Chloride → HCID 19088748, compound

HRID 1463844Notes

Reaction equation

HRID 1463844 reaction equation
[C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[S-:15][C:16]#[N:17].[NH4+].[NH2:19][C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:34]=[CH:33][C:32]3[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=3[CH:26]=2)[N:24]=1>CN(C=O)C.C1COCC1.CC(C)=O.O>[C:1]1([C:11]([NH:17][C:16]([NH:19][C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:34]=[CH:33][C:32]4[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=4[CH:26]=3)[N:24]=2)=[S:15])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 312ChlorideHCID 68471-Naphthoic acidHCID 15666Ammonium thiocyanateHCID 7350914-(5,6,7,8-Tetrahydronaphthalen-2-yl)-1,3-thiazol-2-amine

Product 1

HCID 19088748HCID 19088748, compoundYield 45.4%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 180AcetoneSolvent3×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

DMF (1 drop) was added to a solution of 1-naphthoic acid (900 mg) in THF (10 ml), followed by addition of oxayly chloride (0.49 ml) and stirring at room temperature for 2 hours. After replacing the solvent with acetone (10 ml), a solution of ammonium thiocyanate (436 mg) in acetone (5 ml) was added to the solution, followed by heating over a warm water bath for 1 minute and stirring at room temperature for 20 minutes. Then, a solution of 2-amino-4-(5,6,7,8-tetrahydro-2-naphthyl)thiazole (1,00 g) in acetone (10 ml) was added to the mixed solution, which was then stirred at room temperature for 16 hours. The reaction solution was poured into water, and the crystals which separated out were recovered by filtration and washed with diethyl ether. Recrystallization from dichloroethane-ethanol produced 1-(1-naphthoyl)-3-[4-(5,6,7,8-tetrahydro-2-naphthyl)-2-thiazolyl]thiourea (yield of 875 mg, 45.4%) in the form of colorless needles. m.p. 216°-217° C.

Workup

  1. temperatureby heating over a warm water bath for 1 minute
  2. stirringstirring at room temperature for 20 minutes
  3. stirringwas then stirred at room temperature for 16 hours
  4. customthe crystals which separated out
  5. filtrationwere recovered by filtration
  6. washwashed with diethyl ether
  7. customRecrystallization from dichloroethane-ethanol

Sources & evidence

ORD record
ord-191cd670c6804b1ead7a1d542bb0b7f9
Source dataset
uspto-grants-1994_04
Patent number
US05302608

Reaction notes

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