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

HRID 233703Notes

Reaction equation

HRID 233703 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:

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-9789f98d90374e13ba46f9afae87aaf2
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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