1-(2-Isothiocyanatoethyl)cyclohex-1-ene → N-(2-[1-cyclohexenyl]ethyl)-N'-[(4-isopropyl)pyridinyl]thiourea

HRID 2257782Notes

Reaction equation

HRID 2257782 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]=[C:17]([CH:19]([CH3:21])[CH3:20])[CH:16]=[CH:15][N:14]=1>CN(C)C=O>[C:1]1([CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]2[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[CH:16]=[CH:15][N:14]=2)=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 27358811-(2-Isothiocyanatoethyl)cyclohex-1-eneHCID 157503904-(Propan-2-yl)pyridin-2-amine

Product 1

HCID 53656361N-(2-[1-cyclohexenyl]ethyl)-N'-[(4-isopropyl)pyridinyl]thioureaYield 25.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(1-cyclohexenyl)ethyl isothiocyanate (0.36 g, 2.2 mmol) and 2-amino-4-isopropylpyridine (0.36 g, 2.2 mmol) in N,N-dimethylformamide (20 mL) was heated at 100° C. for 96 h. The reaction was cooled to room temperature, solvents removed under reduced pressure, taken up in ethyl acetate, washed with 1N aqueous HCl. The organic layer was concentrated and the residue purified by HPLC (elution with hexanes-EtOAc) to afford 169 mg (5.6%) of the titled product: mp 105°-106° C.; IR (KBr, cm-1) 3215, 2931, 1614 1556, 1534, 1487, 1199; 1H NMR (300 MHz, DMSO-d6) δ 11.65 (t, 1H), 10.40 (S, 1H), 8.30 (d, 1H), 7.20 (S, 1H), 6.93 (d, 1H), 5.52 (s, 1H), 3.63 (q, 2H), 2.80 (m, 1H), 2.22 (t, 2H), 1.95 (m, 4H), 1.62-1.42 (m, 4H), 1.18 (d, 6H); MS (FD) m/e 303 (M+); UV (EtOH) 290 nm (ε=17565), 266 nm (ε=18863), 247 nm (ε=15125), 203 nm (ε=23091). Anal. Calcd for C17H25N3S: C, 67.28;H, 8.30; N, 13.85. Found: C, 67.55; H, 8.48; N, 13.94.

Workup

  1. customsolvents removed under reduced pressure
  2. washwashed with 1N aqueous HCl
  3. concentrationThe organic layer was concentrated
  4. customthe residue purified by HPLC (elution with hexanes-EtOAc)

Sources & evidence

ORD record
ord-1e4218624a1e4ae4bbde7712d7b0eed0
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

Loading…