Phosphorus oxychloride → 4-chloroquinazolin-2-amine

HRID 973563Notes

Reaction equation

HRID 973563 reaction equation
[NH2:1][C:2]1[NH:11][C:10](=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:15])=O>>[NH2:1][C:2]1[N:11]=[C:10]([Cl:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354038142-Amino-3H-quinazolin-4-one

Product 1

HCID 104422884-chloroquinazolin-2-amineYield 19%

Procedure

2-Amino-4-(3H)-quinazolone (2.0 g, 0.0124 mol) was heated under reflux in phosphoryl chloride (19.02 g, 0.0124 mol) for 2.5 hours. The reaction mixture was partitioned between chloroform, ice and NaOH solution (pH 9) and the organic phase dried, filtered, excess solvent removed and the residue triturated with chloroform to give 2-amino-4-chloroquinazoline (0.42 g, 19%) m.p. 275°-278°.

Workup

  1. customThe reaction mixture was partitioned between chloroform, ice and NaOH solution (pH 9)
  2. customthe organic phase dried
  3. filtrationfiltered
  4. customexcess solvent removed
  5. customthe residue triturated with chloroform

Sources & evidence

ORD record
ord-a00b58d881d04dd3ad21ea4e7e30bf0e
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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