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

HRID 2257772Notes

Reaction equation

HRID 2257772 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.; IR (KBr, cm-1) 3219, 2921, 1605, 1569, 1537, 1481, 1319, 1235, 1181, 1092; 1H NMR (300 MHZ, DMSO-d6) δ 11.55 (s, 1H), 10.47 (s, 1H), 8.09 (d, J=3.9 Hz, 1H), 7.74-7.68 (m, 1H), 7.09 (d, J=8.3 Hz, 1H), 7.00-6.96 (m, 1H), 5.47 (s, 1H), 3.65-3.59 (m, 2H), 2.19 (t, J=6.6 Hz, 2H), 1.94-1.90 (m, 4H), 1.55-1.43 (m, 4H); MS (FD) m/e 261 (M+); UV (EtOH) 292 nm (ε=15926), 265 nm (ε=17724), 247 nm (ε=15198). Anal. Calcd for C14H19N3S: C, 64.33; H, 7.33; N, 16.08. Found: C, 64.12; H, 7.33; N, 15.89.

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-8498bf2518fc4b26abe0f9a17602c62a
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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