Toluene → HCID 21891220, compound

HRID 721885Notes

Reaction equation

HRID 721885 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([N:10]=[C:11]=[S:12])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][C:29]=1[CH3:35].C1(C)C=CC=CC=1>C(O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[N:21]=[CH:20][CH:19]=[C:18]2[O:27][C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:11]([NH:10][C:8](=[O:9])[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[S:12])=[CH:30][C:29]=1[CH3:35]

Participants

5

Reactant 3

HCID 1140TolueneHCID 1413973-Methylbenzoyl isothiocyanateHCID 218911624-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methyl-aniline

Product 1

HCID 21891220HCID 21891220, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Commercially available 3-methyl-1-benzenecarbonyl isothiocyanate (50 μl) was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methylaniline (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 (65 mg, yield 83%).

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-77eb708bae1042deb0ecbe3c185b014b
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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