Dimethylformamide → 7-(Benzyloxy)-4-chloroquinazoline

HRID 640004Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.S(Cl)([Cl:27])=O>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:27])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24386Thionyl Chloride

HCID 1357631107-(Benzyloxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 220309237-(Benzyloxy)-4-chloroquinazolineYield 90%

Conditions

Temperature: 90 °C

Procedure

A solution of 7-(benzyloxy)quinazolin-4(3H)-one (5.0 g, 19.8 mmol) in thionyl chloride (40 ml) containing a catalytic amount of dimethylformamide was heated at 90° C. for 2 hours. The solvent was concentrated in vacuo and the oily residue co-evaporated with toluene (2×100 ml) to leave a yellow solid which was triturated with diethyl ether to yield 7-(benzyloxy)4-chloroquinazoline (4.79 g, 90% yield) as a pale yellow solid:

Workup

concentrationThe solvent was concentrated in vacuo
customthe oily residue co-evaporated with toluene (2×100 ml) to leave a yellow solid which
customwas triturated with diethyl ether

Sources & evidence

ORD record: ord-de0a66b5d15546f1b4fa21bd5e347510
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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