Dimethylformamide → 4-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline

HRID 1386249Notes

Reaction equation

HRID 1386249 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][O:21][CH3:22])[N:14]=[CH:13][NH:12][C:11]2=O.S(Cl)([Cl:26])=O>>[Cl:26][C:11]1[C:10]2[C:15](=[CH:16][C:17]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:8]([O:7][CH3:6])[CH:9]=2)[N:14]=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 135407708HCID 135407708, compound

Product 1

HCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazolineYield 51%

Procedure

DMF (0.5 ml) was added to a mixture of 6-methoxy-7-(2-methoxyethoxy)3,4-dihydroquinazolin-4-one (5.1 g, 20 mmol) in thionyl chloride (50 ml). The mixture was stirred and heated at reflux for 3 hours, allowed to cool and the excess thionyl chloride removed by evaporation. The residue was suspended in methylene chloride and washed with aqueous sodium hydrogen carbonate solution. The aqueous phase was extracted with methylene chloride and the combined extracts dried (MgSO4). The crude product was recrystallised from methylene chloride/hexane to give 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (2.8 g, 51%) as a fine white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool
  4. customthe excess thionyl chloride removed by evaporation
  5. washwashed with aqueous sodium hydrogen carbonate solution
  6. extractionThe aqueous phase was extracted with methylene chloride
  7. dry with materialthe combined extracts dried (MgSO4)
  8. customThe crude product was recrystallised from methylene chloride/hexane

Sources & evidence

ORD record
ord-8f46683d37cc4e809c5af667b12f0c86
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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