Toluene → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-[{[di(2-chloroethyl)amino]carbonyl}amino]methanethioamide

HRID 721825Notes

Reaction equation

HRID 721825 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].[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][C:32]1[C:41]2[C:36](=[CH:37][C:38]([O:44][CH3:45])=[C:39]([O:42][CH3:43])[CH:40]=2)[N:35]=[CH:34][CH:33]=1)[NH2:27].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].[Cl:23][C:24]1[CH:25]=[C:26]([NH:27][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:28]=[CH:29][C:30]=1[O:31][C:32]1[C:41]2[C:36](=[CH:37][C:38]([O:44][CH3:45])=[C:39]([O:42][CH3:43])[CH:40]=2)[N:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 76346Bis(2-chloroethyl)carbamoyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 21890320[Di(2-chloroethyl)amino]methanoyl isothiocyanate

Product 2

HCID 21890320[Di(2-chloroethyl)amino]methanoyl isothiocyanateHCID 21890691N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-[{[di(2-chloroethyl)amino]carbonyl}amino]methanethioamideYield 60%

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. 3-Chloro-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 (51 mg, yield 60%).

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-ba24d496d5a741cab6b631d571d7368a
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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