Toluene → HCID 21890282, compound

HRID 721821Notes

Reaction equation

HRID 721821 reaction equation
N1(C(Cl)=O)CCOCC1.[N:10]1([C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[O:33][CH3:34])[N:29]=[CH:28][CH:27]=[C:26]2[O:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1.C1(C)C=CC=CC=1>C(O)C>[N:10]1([C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[O:33][CH3:34])[N:29]=[CH:28][CH:27]=[C:26]2[O:35][C:36]1[CH:37]=[CH:38][C:39]([NH:40][C:19]([NH:18][C:16]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[O:17])=[S:20])=[CH:41][CH:42]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 848104-Morpholinecarbonyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 13441037HCID 13441037, compound

Product 2

HCID 13441037HCID 13441037, compoundHCID 21890282HCID 21890282, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Morpholinecarbonyl isothiocyanate was prepared using commercially available 4-morpholinecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-Morpholinecarbonyl 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 (49 mg, yield 62%).

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-154cf824f7ec4f1aac4b7fa442fc6b3a
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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