Toluene → HCID 21890488, compound

HRID 721817Notes

Reaction equation

HRID 721817 reaction equation
C(N(CC)C(Cl)=O)C.[CH2:9]([N:11]([C:14]([N:16]=[C:17]=[S:18])=[O:15])[CH2:12][CH3:13])[CH3:10].[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[N:27]=[CH:26][CH:25]=[C:24]2[O:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1.C1(C)C=CC=CC=1>C(O)C>[CH2:9]([N:11]([C:14]([N:16]=[C:17]=[S:18])=[O:15])[CH2:12][CH3:13])[CH3:10].[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[N:27]=[CH:26][CH:25]=[C:24]2[O:33][C:34]1[CH:35]=[CH:36][C:37]([NH:38][C:17]([NH:16][C:14]([N:11]([CH2:12][CH3:13])[CH2:9][CH3:10])=[O:15])=[S:18])=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6916Diethylcarbamoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 12206212HCID 12206212, compound

Product 2

HCID 12206212HCID 12206212, compoundHCID 21890488HCID 21890488, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

(Diethylamino)methanoyl isothiocyanate was prepared using commercially available N,N-diethylcarbamic chloride (80 mg) as a starting compound according to the description of the literature. (Diethylamino)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 (42 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-e3180b19c4d64ada9d7f077c031edc95
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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