Dichloromethane → HCID 135404741, compound

HRID 634748Notes

Reaction equation

HRID 634748 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][S:19][CH2:18][CH2:17]1)[N:9]=[CH:8][N:7]=[C:6]2[O:22]C1C=CC=CC=1.C(=O)([O-])O.[Na+].C(Cl)Cl>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][S:19][CH2:18][CH2:17]1)[N:9]=[CH:8][NH:7][C:6]2=[O:22]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 21260335HCID 21260335, compound

Product 1

HCID 135404741HCID 135404741, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-methoxy-4-phenoxy-7-(2-thiomorpholinoethoxy)quinazoline (2.0 g, 5 mmol) in 2M hydrochloric acid (25 ml) was heated at 90° C. for 1.5 hours. The mixture was allowed to cool and adjusted to pH7 with solid sodium hydrogen carbonate. Methylene chloride was added and the resulting semi-solid product was isolated by decanting and filtering the aqueous mixture. This product was dissolved in acetone and insoluble material was removed by filtration. The solvent was removed by evaporation and the residue azeotroped with toluene to give 6-methoxy-7-(2-thiomorpholinoethoxy)-3,4-dihydroquinazolin-4-one (1.5 g, 92%) as a white solid.

Workup

  1. temperatureto cool
  2. customthe resulting semi-solid product was isolated
  3. customby decanting
  4. filtrationfiltering the aqueous mixture
  5. dissolutionThis product was dissolved in acetone
  6. custominsoluble material was removed by filtration
  7. customThe solvent was removed by evaporation
  8. customthe residue azeotroped with toluene

Sources & evidence

ORD record
ord-2ec2a243d89349e9af0479ddb650bd1f
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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