Phosphorus oxychloride → 4-Chloro-2-(5-chloro-2-fluorophenyl)-5,6,7,8-tetrahydroquinazoline

HRID 1010855Notes

Reaction equation

HRID 1010855 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([C:8]2[N:17]=[C:16](O)[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[N:9]=2)[CH:7]=1.C([O-])(O)=O.[Na+].O=P(Cl)(Cl)[Cl:27]>C(Cl)Cl>[Cl:27][C:16]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[N:9]=[C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[F:19])[N:17]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178517509HCID 178517509, compound

Product 1

HCID 211043374-Chloro-2-(5-chloro-2-fluorophenyl)-5,6,7,8-tetrahydroquinazoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-(5-chloro-2-fluorophenyl)-5,6,7,8-tetrahydroquinazolin-4-ol (500 mg, 1.89 mmol) in POCl3 (6 ml) was stirred under reflux for 1 h. The solution was then cooled to room temperature and concentrated under reduced pressure to afford a white solid which was dissolved in methylene chloride. The solution was cooled to 0° C. and ice was added followed by sat. NaHCO3. The organic layer was separated, washed with brine, dried (MgSO4), filtered and evaporated in vacuo to provide a crude white solid 4-Chloro-2-(5-chloro-2-fluorophenyl)-5,6,7,8-tetrahydroquinazoline which was not further purified.

Workup

  1. temperatureunder reflux for 1 h
  2. concentrationconcentrated under reduced pressure
  3. customto afford a white solid which
  4. temperatureThe solution was cooled to 0° C.
  5. additionice was added
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-e552d52445b647e2b466e5752b76fe18
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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