Toluene → HCID 21890356, compound

HRID 721812Notes

Reaction equation

HRID 721812 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])=[C:36]([F:41])[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:40]=[CH:39][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])=[C:36]([F:41])[CH:35]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 27763773-Thenoyl chlorideHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroanilineHCID 21890437HCID 21890437, compound

Product 2

HCID 21890356HCID 21890356, compoundYield 58%HCID 21890437HCID 21890437, compound

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]-2-fluoroaniline (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 58%).

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-a465f1c476714abb8865cd293d68c6a6
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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