Toluene → HCID 21890964, compound

HRID 721786Notes

Reaction equation

HRID 721786 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](Cl)=[O:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:24]([N:26]=[C:27]=[S:28])=[O:25])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][C:40]=1[O:41][CH3:42])[N:37]=[CH:36][CH:35]=[C:34]2[O:43][C:44]1[CH:50]=[CH:49][C:47]([NH2:48])=[CH:46][CH:45]=1.C1(C)C=CC=CC=1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([N:26]=[C:27]=[S:28])=[O:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:24]([NH:26][C:27]([NH:48][C:47]1[CH:49]=[CH:50][C:44]([O:43][C:34]2[C:33]3[C:38](=[CH:39][C:40]([O:41][CH3:42])=[C:31]([O:30][CH3:29])[CH:32]=3)[N:37]=[CH:36][CH:35]=2)=[CH:45][CH:46]=1)=[S:28])=[O:25]

Participants

7

Reactant 4

HCID 1140TolueneHCID 870033,5-Dimethoxybenzoyl chlorideHCID 2119218HCID 2119218, compoundHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 2

HCID 21890908HCID 21890908, compoundHCID 21890964HCID 21890964, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3,5-Dimethoxy-1-benzenecarbonyl isothiocyanate was prepared using commercially available 3,5-dimethoxy-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 3,4-Dimethoxy-1-benzenecarbonyl 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 (70 mg, yield 80%).

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-fbbcc28f6fc64c539134aa4c5d3dd0f8
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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