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

HRID 241348Notes

Reaction equation

HRID 241348 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-2fba46a884c24af3a0fd9ac94ead7ba4
Source dataset
uspto-grants-2014_02
Patent number
US08648197B2

Reaction notes

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