Veratroyl chloride → HCID 21890424, compound

HRID 721955Notes

Reaction equation

HRID 721955 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][N:20]=[C:19]2[O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1.[CH3:36][O:37][C:38]1[CH:39]=[C:40]([C:46]([N:48]=[C:49]=[S:50])=[O:47])[CH:41]=[CH:42][C:43]=1[O:44][CH3:45]>C1(C)C=CC=CC=1.C(O)C>[CH3:36][O:37][C:38]1[CH:39]=[C:40]([C:46]([N:48]=[C:49]=[S:50])=[O:47])[CH:41]=[CH:42][C:43]=1[O:44][CH3:45].[CH3:36][O:37][C:38]1[CH:39]=[C:40]([CH:41]=[CH:42][C:43]=1[O:44][CH3:45])[C:46]([NH:48][C:49]([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][N:20]=2)=[CH:30][CH:31]=1)=[S:50])=[O:47]

Participants

7

Reactant 3

HCID 77070Veratroyl chlorideHCID 2119218HCID 2119218, compoundHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)aniline

Product 2

HCID 2119218HCID 2119218, compoundHCID 21890424HCID 21890424, compoundYield 65%

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-quinazolinyl)oxy]aniline (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 (57 mg, yield 65%).

Workup

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

Sources & evidence

ORD record
ord-b10567cde9e4415a9a0eaa1f868e1d7f
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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