Bromoacetyl chloride → 6-(2-Bromoacetyl)-3,4-dihydro-4-methyl-2(1H)-quinazolinone

HRID 979058Notes

Reaction equation

HRID 979058 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9](=[O:17])[NH:8]1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Br:1][CH2:2][C:3]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:17])[NH:8][CH:7]2[CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 123607574-Methyl-3,4-dihydro-1H-quinazolin-2-one

Product 1

HCID 138271676-(2-Bromoacetyl)-3,4-dihydro-4-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

2-Bromoacetyl chloride (9.7 g) is added dropwise to a stirred mixture of 3,4-dihydro-4-methyl-2(1H)-quinazolinone (5 g), anhydrous aluminum chloride (10.3 g) and carbon disulfide (100 ml) under nitrogen. The reaction mixture is refluxed for about 18 hours, the carbon disulfide decanted, and the residue treated with hydrochloric acid (6N) and ethyl acetate. The layers are separated, and the aqueous layer extracted with ethyl acetate and the combined ethyl acetate extracts washed with sat'd. aqueous sodium bicarbonate and water and dried. The dried organic extract is filtered and the filtrate evaporated, affording the desired product as a solid, which is used without further purification, M.P. 188°-190° C.

Workup

  1. temperatureThe reaction mixture is refluxed for about 18 hours
  2. customthe carbon disulfide decanted
  3. additionthe residue treated with hydrochloric acid (6N) and ethyl acetate
  4. customThe layers are separated
  5. extractionthe aqueous layer extracted with ethyl acetate
  6. washthe combined ethyl acetate extracts washed with sat'd
  7. dry with materialaqueous sodium bicarbonate and water and dried
  8. extractionThe dried organic extract
  9. filtrationis filtered
  10. customthe filtrate evaporated

Sources & evidence

ORD record
ord-23fbc969c7b541e596df8367f33737b4
Source dataset
uspto-grants-1987_05
Patent number
US04666913

Reaction notes

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