Chlorine monoxide → 7-Bromo-4-chloro-2-methylquinazoline

HRID 914926Notes

Reaction equation

HRID 914926 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.O(Cl)[Cl:15]>CN(C)C1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:15])=[N:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24646Chlorine monoxideHCID 1358045037-Bromo-2-methylquinazolin-4(3H)-one

Product 1

HCID 222478197-Bromo-4-chloro-2-methylquinazolineYield 59%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 0.45 g 7-bromo-2-methyl-3H-quinazolin-4-one in 0.48 ml N,N-dimethylaniline is treated with 1.41 ml phosphourous oxychloride and heated at 60° C. for 2 h. The reaction mixture is evaporated in vacuo and the residue is taken up with 20 ml water, neutralized with 10 ml saturated aqueous sodium bicarbonate and extracted with 25 ml dichloromethane twice. The organic layer is washed with 25 ml water, 25 ml brine, dried over magnesium sulfate and evaporated in vacuo. The residue is purified by chromatography on silica gel with Heptane/ethylacetate 2:1. 0.288 g (59%) of 7-bromo-4-chloro-2-methyl-quinazoline are obtained as an orange solid. Mp. >82° C. (dec). MS (EI): peaks at m/e: 258(M+, 37%), 221 (100%), 179(9%).

Workup

  1. customThe reaction mixture is evaporated in vacuo
  2. extractionextracted with 25 ml dichloromethane twice
  3. washThe organic layer is washed with 25 ml water, 25 ml brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue is purified by chromatography on silica gel with Heptane/ethylacetate 2:1

Sources & evidence

ORD record
ord-d32028c086184d7a8a0cf3c45fc0c418
Source dataset
uspto-grants-2007_09
Patent number
US07265125B2

Reaction notes

Loading…