2-Mercaptoethanol → 6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethylthiomethyl)quinazoline

HRID 862621Notes

Reaction equation

HRID 862621 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]([O:25][CH3:26])=[C:8]([O:23][CH3:24])[CH:9]=2)[N:4]=1.[SH:27][CH2:28][CH2:29][OH:30].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:24][O:23][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[O:25][CH3:26])[N:4]=[C:3]([CH2:2][S:27][CH2:28][CH2:29][OH:30])[N:12]=[C:11]2[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 107856562-Chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline

Product 1

HCID 218511326,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethylthiomethyl)quinazolineYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline (4.5 g), 2-mercaptoethanol (1.13 g), potassium carbonate (2.8 g) and N,N-dimethylformamide (50 ml) was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethylthiomethyl)quinazoline (4.1 g, 82%) which was then recrystallized from ethanol. Colorless prisms. mp. 154°-155° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3990580e032643fbabf51743fd174847
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

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