Toluene → N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(2-methylpentanoyl)thiourea

HRID 721953Notes

Reaction equation

HRID 721953 reaction equation
[CH3:1][CH:2]([CH2:8][CH2:9][CH3:10])[C:3]([N:5]=[C:6]=[S:7])=[O:4].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][N:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.C1(C)C=CC=CC=1>C(O)C>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][N:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:6]([NH:5][C:3](=[O:4])[CH:2]([CH3:1])[CH2:8][CH2:9][CH3:10])=[S:7])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 218904792-Methylpentanoyl isothiocyanate

Product 1

HCID 21890971N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(2-methylpentanoyl)thioureaYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Methylpentanoyl isothiocyanate prepared according to the method 2 was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinazolinyl)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 16 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 (44 mg, yield 57%).

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-b783f78d4e1d4f4988e227eefa92166d
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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