1,2-Dichloroethane → 4-Chloro-6-methoxyquinazoline

HRID 1920113Notes

Reaction equation

HRID 1920113 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][NH:7][C:6]2=O.[Cl:14]CCCl.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Cl:14][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24819Phosphorus pentachlorideHCID 1354514236-Methoxyquinazolin-4-OL

Product 1

HCID 111831744-Chloro-6-methoxyquinazolineYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.852 mmoles of 6-methoxy-3H-quinazolin-4-one in 0.4M soln of DCE, add 1.022 mmoles of PCl5. Microwave at 150° C. for 4000 secs. Work-up: The reaction mixture was diluted with CH2Cl2 and washed with water and brine. The organic layer was separated dried over MgSO4, filtered and excess solvent was removed on rotavap to yield the title compound in 75% yield. The compound was used for the next step without further purification. LC-MS: m/z=195 (M++1)

Workup

  1. washwashed with water and brine
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customexcess solvent was removed on rotavap

Sources & evidence

ORD record
ord-81b99d7a06f846708c51dec84e5afb80
Source dataset
uspto-grants-2012_05
Patent number
US08168788B2

Reaction notes

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