Phosphorus oxychloride → 7-Bromo-4-chloroquinazoline

HRID 2274142Notes

Reaction equation

C(N(C(C)C)C(C)C)C.[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=O)[NH:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1.O=P(Cl)(Cl)[Cl:24]>>[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([Cl:24])=[N:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 81531Diisopropylethylamine

HCID 1355556127-Bromo-3,4-dihydroquinazolin-4-one

Product 1

HCID 167808557-Bromo-4-chloroquinazoline

Conditions

Temperature: 115 °C

Procedure

20.4 ml (0.12 mol) of N-ethyldiisopropylamine were slowly added to a suspension of 55.0 g (0.24 mol) of 7-bromo-3H-quinazolin-4-one in 300 ml of phosphorus oxytrichloride. The reaction mixture was stirred at 115° C. for 3 h and subsequently allowed to come to room temperature. Conventional work-up gave 48.0 g of 7-bromo-4-chloroquinazoline; HPLC/MS (M+H)+=244 as solid.

Workup

customto come to room temperature

Sources & evidence

ORD record: ord-88fedd410b7a4977b1c1eba90365a769
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126952B2

Reaction notes

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