Toluene → HCID 21891140, compound

HRID 721829Notes

Reaction equation

HRID 721829 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.[Cl:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:32]=1[O:33][C:34]1[C:43]2[C:38](=[CH:39][C:40]([O:46][CH3:47])=[C:41]([O:44][CH3:45])[CH:42]=2)[N:37]=[CH:36][CH:35]=1)[NH2:29].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.[Cl:25][C:26]1[CH:27]=[C:28]([NH:29][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:30]=[CH:31][C:32]=1[O:33][C:34]1[C:43]2[C:38](=[CH:39][C:40]([O:46][CH3:47])=[C:41]([O:44][CH3:45])[CH:42]=2)[N:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 13441039HCID 13441039, compound

Product 2

HCID 13441039HCID 13441039, compoundHCID 21891140HCID 21891140, compoundYield 71%

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. 3-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 (56 mg, yield 71%).

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-c5d99d2cd1bd4bd289880bc1356bc552
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…