Toluene → HCID 21891059, compound

HRID 721822Notes

Reaction equation

HRID 721822 reaction equation
CN(C1C=CC=CC=1)C(Cl)=O.[CH3:12][N:13]([C:20]([N:22]=[C:23]=[S:24])=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[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])=[CH:42][CH:41]=1.C1(C)C=CC=CC=1>C(O)C>[CH3:12][N:13]([C:20]([N:22]=[C:23]=[S:24])=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[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:41]=[CH:42][C:43]([NH:44][C:23]([NH:22][C:20]([N:13]([CH3:12])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:21])=[S:24])=[CH:45][CH:46]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 13441039HCID 13441039, compound

Product 2

HCID 13441039HCID 13441039, compoundHCID 21891059HCID 21891059, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

(Methylanilino)methanoyl isothiocyanate was prepared using commercially available N-methyl-N-phenylcarbamic chloride (80 mg) as a starting compound according to the description of the literature. (Methylanilino)methanoyl 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 (52 mg, yield 63%).

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-3de274b8ce034aca87560ff922367cdf
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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