Toluene → HCID 21890835, compound

HRID 721870Notes

Reaction equation

HRID 721870 reaction equation
COC1C=CC(C(Cl)=O)=CC=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([N:22]=[C:23]=[S:24])=[O:21])=[CH:16][CH:15]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][C:36]=1[O:37][CH3:38])[N:33]=[CH:32][CH:31]=[C:30]2[O:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[C:42]([CH3:47])[CH:41]=1.C1(C)C=CC=CC=1>C(O)C>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([N:22]=[C:23]=[S:24])=[O:21])=[CH:18][CH:19]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][C:36]=1[O:37][CH3:38])[N:33]=[CH:32][CH:31]=[C:30]2[O:39][C:40]1[CH:46]=[CH:45][C:43]([NH:44][C:23]([NH:22][C:20](=[O:21])[C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=2)=[S:24])=[C:42]([CH3:47])[CH:41]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7477p-Anisoyl chlorideHCID 1401364-Methoxybenzoyl isothiocyanateHCID 218905104-((6,7-Dimethoxyquinolin-4-yl)oxy)-2-methylaniline

Product 2

HCID 1401364-Methoxybenzoyl isothiocyanateHCID 21890835HCID 21890835, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Methoxy-1-benzenecarbonyl isothiocyanate was prepared using commercially available 4-methoxy-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-Methoxy-1-benzenecarbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-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 (37 mg, yield 45%).

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-f80aa794cce04526ae5d10ce45ec6e9e
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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