Veratroyl chloride → HCID 21890778, compound

HRID 721846Notes

Reaction equation

HRID 721846 reaction equation
COC1C=C(C(Cl)=O)C=CC=1OC.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[N:22]=[CH:21][CH:20]=[C:19]2[O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][C:30]=1[F:36].[CH3:37][O:38][C:39]1[CH:40]=[C:41]([C:47]([N:49]=[C:50]=[S:51])=[O:48])[CH:42]=[CH:43][C:44]=1[O:45][CH3:46]>C1(C)C=CC=CC=1.C(O)C>[CH3:37][O:38][C:39]1[CH:40]=[C:41]([C:47]([N:49]=[C:50]=[S:51])=[O:48])[CH:42]=[CH:43][C:44]=1[O:45][CH3:46].[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[C:47]([NH:49][C:50]([NH:33][C:32]1[CH:34]=[CH:35][C:29]([O:28][C:19]2[C:18]3[C:23](=[CH:24][C:25]([O:26][CH3:27])=[C:16]([O:15][CH3:14])[CH:17]=3)[N:22]=[CH:21][CH:20]=2)=[C:30]([F:36])[CH:31]=1)=[S:51])=[O:48]

Participants

7

Reactant 3

HCID 77070Veratroyl chlorideHCID 2119218HCID 2119218, compoundHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamine

Product 2

HCID 2119218HCID 2119218, compoundHCID 21890778HCID 21890778, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

3,4-Dimethoxy-1-benzenecarbonyl isothiocyanate was prepared using commercially available 3,4-dimethoxy-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluoroaniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 3,4-dimethoxy-1-benzenecarbonyl isothiocyanate in ethanol (1 ml) was then 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 (54 mg, yield 63%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9d269197d95d40be9d62c707117caa41
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…