Ethyl Acetate → N-(2-(1-Cyclohexenyl)ethyl)-N'-[2-pyridyl]thiourea

HRID 861589Notes

Reaction equation

HRID 861589 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]=[C:10]=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(OCC)(=O)C>CN1CCCC1=O>[C:1]1([CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 104392-AminopyridineHCID 27358811-(2-Isothiocyanatoethyl)cyclohex-1-ene

Product 1

HCID 3000476N-(2-(1-Cyclohexenyl)ethyl)-N'-[2-pyridyl]thioureaYield 50.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-(1-cyclohexenyl)ethyl isothiocyanate (1.67 g, 10 mmol) and 2-aminopyridine (941 mg, 10 mmol) in N-methylpyrrolidinone (20 mL) was heated to 100° C. After 16.5 h, the reaction was cooled to room temperature and poured into ethyl acetate. The organic phase was washed with water (4×) and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The solid obtained was purified by recrystallization from ethyl acetate to provide 1.31 g of the titled product (50%) as a white crystalline solid: mp 153°-155° C.;

Workup

  1. washThe organic phase was washed with water (4×) and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe solid obtained
  6. customwas purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f95e3545deb14d72a6da2df27e095848
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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