Propanoyl bromide, 2-bromo- → 6-(2-Bromopropionyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

HRID 979057Notes

Reaction equation

HRID 979057 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].[CH3:7][N:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:18].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Br:1][CH:2]([CH3:6])[C:3]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:18])[N:8]([CH3:7])[CH2:17]2)=[O:4]

Participants

5

Reactant 3

HCID 79047Propanoyl bromide, 2-bromo-HCID 38465583,4-Dihydro-3-methyl-2(1H)-quinazolinoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 138271666-(2-Bromopropionyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

2-Bromopropionyl bromide (6.7 g) is added dropwise to a stirring mixture of 3,4-dihydro-3-methyl-2(1H)-quinazolinone (2.5 g) and anhydrous aluminum chloride (4.9 g) in carbon disulfide (50 ml) under nitrogen. The reaction mixture is refluxed for five hours, cooled to RT, the carbon disulfide decanted, and the residue treated with hydrochloric acid (6N). The treated residue is poured into ice water, and the resulting suspension is stirred, filtered, the filtered solid washed with water, and dried in vacuo, affording the desired product, which is used in the next step without further purification, M.P. 150°-165° C. (dec).

Workup

  1. temperatureThe reaction mixture is refluxed for five hours
  2. customthe carbon disulfide decanted
  3. additionthe residue treated with hydrochloric acid (6N)
  4. additionThe treated residue is poured into ice water
  5. filtrationfiltered
  6. washthe filtered solid washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-9da76f7a64844b85b6eca56b74afeecd
Source dataset
uspto-grants-1987_05
Patent number
US04666913

Reaction notes

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