Toluene → HCID 21890503, compound

HRID 721882Notes

Reaction equation

HRID 721882 reaction equation
[C:1]1([C:7]([N:9]=[C:10]=[S:11])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][C:13]1[CH:19]=[C:18]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][C:14]=1[NH2:15].C1(C)C=CC=CC=1>C(O)C>[C:7]([NH:9][C:10]([NH:15][C:14]1[CH:16]=[CH:17][C:18]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][CH:22]=2)=[CH:19][C:13]=1[Cl:12])=[S:11])(=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 68284Benzoyl isothiocyanateHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

Product 1

HCID 21890503HCID 21890503, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Commercially available 1-benzenecarbonyl isothiocyanate (50 μl) was dissolved in ethanol (1 ml) to prepare a solution. 2-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 (36 mg, yield 48%).

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-e963a320f6c64f54b973947ac0d76a47
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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