Toluene → HCID 21890560, compound

HRID 721810Notes

Reaction equation

HRID 721810 reaction equation
S1C=CC(C(Cl)=O)=C1.[S:9]1[CH:13]=[CH:12][C:11]([C:14]([N:16]=[C:17]=[S:18])=[O:15])=[CH:10]1.[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>[S:9]1[CH:13]=[CH:12][C:11]([C:14]([N:16]=[C:17]=[S:18])=[O:15])=[CH:10]1.[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]([C:11]2[CH:12]=[CH:13][S:9][CH:10]=2)=[O:15])=[S:18])=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 27763773-Thenoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 21890437HCID 21890437, compound

Product 2

HCID 21890437HCID 21890437, compoundHCID 21890560HCID 21890560, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-Thiophenecarbonyl isothiocyanate was prepared using commercially available 3-thiophenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 3-Thiophenecarbonyl 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 (45 mg, yield 68%).

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-bab4f12a19354b0895eea72a0ea79c97
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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