Toluene → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-[{[di(2-chloroethyl)amino]carbonyl}amino]methanethioamide

HRID 721818Notes

Reaction equation

HRID 721818 reaction equation
ClCCN(CCCl)C(Cl)=O.[Cl:11][CH2:12][CH2:13][N:14]([C:18]([N:20]=[C:21]=[S:22])=[O:19])[CH2:15][CH2:16][Cl:17].[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:34]=1[O:35][CH3:36])[N:31]=[CH:30][CH:29]=[C:28]2[O:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1.C1(C)C=CC=CC=1>C(O)C>[Cl:17][CH2:16][CH2:15][N:14]([C:18]([N:20]=[C:21]=[S:22])=[O:19])[CH2:13][CH2:12][Cl:11].[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:34]=1[O:35][CH3:36])[N:31]=[CH:30][CH:29]=[C:28]2[O:37][C:38]1[CH:39]=[CH:40][C:41]([NH:42][C:21]([NH:20][C:18]([N:14]([CH2:13][CH2:12][Cl:11])[CH2:15][CH2:16][Cl:17])=[O:19])=[S:22])=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 76346Bis(2-chloroethyl)carbamoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 21890320[Di(2-chloroethyl)amino]methanoyl isothiocyanate

Product 2

HCID 21890320[Di(2-chloroethyl)amino]methanoyl isothiocyanateHCID 21890592N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-[{[di(2-chloroethyl)amino]carbonyl}amino]methanethioamideYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

[Di(2-chloroethyl)amino]methanoyl isothiocyanate was prepared using commercially available N,N-di(2-chloroethyl)carbamic chloride (80 mg) as a starting compound according to the description of the literature. [Di(2-chloroethyl)amino]methanoyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg), toluene (5 ml), and ethanol (1 ml) were 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 (48 mg, yield 55%).

Workup

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

Sources & evidence

ORD record
ord-16fca321b0cc4e8fa58a92e53dc66172
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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