Chloroform → 2,5-Dichloroquinazolin-8-ol

HRID 2079655Notes

Reaction equation

[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(Cl)(Cl)[Cl:14]>>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][C:8]=2[Cl:14])[N:3]=1

Participants

Reactant 2

HCID 6212Chloroform

HCID 591992302-Chloro-8-quinazolinol

Product 1

HCID 591992212,5-Dichloroquinazolin-8-olYield 65%

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-chloroquinazolin-8-ol (1 eq) in chloroform was added N-chlosuccinimide (1 eq) and the resulting mixture was heated to 40° C. for 2 h. The chlorination goes to completion giving 2,5-dichloroquinazolin-8-ol in 65% yield. 25% of the reaction was 2,7-dichloroquinazolin-8-ol and 15% of the reaction mixture was 2,5,8-trichloro quinazolin-8-ol. The reaction mixture was concentrated and the crude was purified by silica gel. The structures of the isomers were confirmed by 1H NMR and by LC/MS. ES/MS m/z 215 (MH+).

Sources & evidence

ORD record: ord-1a3528b187054132b0415eb5187354a5
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932262B2

Reaction notes

Loading…