Phosphorus oxychloride → 4-Chloroquinazolin-2-amine

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

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 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

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

Sources & evidence

ORD record: ord-a00b58d881d04dd3ad21ea4e7e30bf0e
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05064833

Reaction notes

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