Phenylacetyl chloride → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethyl-N'-(2-phenylacetyl)thiourea

HRID 721922Notes

Reaction equation

HRID 721922 reaction equation
C1(CC(Cl)=O)C=CC=CC=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][CH:17]=[C:16]2[O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][CH2:33][CH3:34])=[CH:28][CH:27]=1.[C:35]1([CH2:41][C:42]([N:44]=[C:45]=[S:46])=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1(C)C=CC=CC=1.C(O)C>[C:35]1([CH2:41][C:42]([N:44]=[C:45]=[S:46])=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][CH:17]=[C:16]2[O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]([CH2:33][CH3:34])[C:45]([NH:44][C:42](=[O:43])[CH2:41][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[S:46])=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 12454157Phenylacetyl isothiocyanateHCID 21891226N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethylamine

Product 2

HCID 12454157Phenylacetyl isothiocyanateHCID 21890890N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethyl-N'-(2-phenylacetyl)thioureaYield 48%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

2-Phenylethanoyl isothiocyanate was prepared using commercially available 2-phenylethanoyl chloride (80 mg) as a starting compound according to the description of the literature. N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethylamine (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 2-phenylethanoyl isothiocyanate in ethanol (1 ml) was then added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (38 mg, yield 48%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-208e0798d67c46f8a3da0f3164ad837b
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…