Ethanol → HCID 86751106, compound

HRID 266154Notes

Reaction equation

HRID 266154 reaction equation
ClC[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.[CH2:27]([NH2:29])[CH3:28].[CH2:30](O)C>ClCCl>[CH2:27]([NH:29][CH2:30][N:4]1[C:5]2[C:10](=[CH:9][C:8]([O:23][CH3:24])=[C:7]([O:25][CH3:26])[CH:6]=2)[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)=[N:12][CH2:3]1)[CH3:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 6341EthylamineHCID 107856562-Chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline

Product 1

HCID 86751106HCID 86751106, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (10.0 g), ethylamine (70% aqueous solution, 206 g) and ethanol (200 ml)--dichloromethane (200 ml) was stirred at room temperature for 13 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in dichloromethane. The dichloromethane layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform - ethanol (5:1, v/v) gave 2-(N-ethylaminomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (5.7 g, 55%). This compound was recrystallized from ethanol. Colorless prisms, mp. 128°-130° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe dichloromethane layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe fractions eluted with chloroform - ethanol (5:1

Sources & evidence

ORD record
ord-f4cf7c793068498eb61f0ff4082f44c9
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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