Chloride → HCID 54355284, compound

HRID 1463845Notes

Reaction equation

HRID 1463845 reaction equation
[Cl-].[S-:2][C:3]#[N:4].[K+].[NH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:21]=[CH:20][C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=2)[N:11]=1.[OH2:22]>O1CCOCC1>[CH2:10]([CH:12]([CH2:13][CH2:14][CH2:19][CH3:18])[C:21]([NH:4][C:3]([NH:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:21]=[CH:20][C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=2)[N:11]=1)=[S:2])=[O:22])[CH3:9]

Participants

6

Reactant 4

HCID 312ChlorideHCID 962WaterHCID 516872Potassium thiocyanateHCID 7350914-(5,6,7,8-Tetrahydronaphthalen-2-yl)-1,3-thiazol-2-amine

Product 1

HCID 54355284HCID 54355284, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Ethylexanoyl chloride (0.43 g) was added to a solution of potassium thiocyanate (0.506 g) in dioxane (10 ml), followed by stirring at 55° to 60° C. for 4 hours. Then, 2-amino-4-(5,6,7,8-tetrahydro-2-naphthyl)thiazole (0.5 g) was added to the solution, which was stirred at 55° to 60° C. for 3 hours. The reaction mixture was poured into water, and the crystals which separated out were recovered by filtration, washed with water and isopropyl ether, successively, and recrystallized from dichloromethane-isopropyl ether to give 1-(2-ethylhexanoyl) 3-[4-(5,6,7,8-tetrahydro-2-naphthyl)-2-thiazolyl]thiourea (0.438 g, 58.1%) in the form of colorless needles. m.p. 178°-179° C.

Workup

  1. stirringwas stirred at 55° to 60° C. for 3 hours
  2. customthe crystals which separated out
  3. filtrationwere recovered by filtration
  4. washwashed with water and isopropyl ether
  5. customsuccessively, and recrystallized from dichloromethane-isopropyl ether

Sources & evidence

ORD record
ord-d46cc94b3dbc4bbd8cb9467c867f2f7a
Source dataset
uspto-grants-1994_04
Patent number
US05302608

Reaction notes

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