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

HRID 979055Notes

Reaction equation

HRID 979055 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].[NH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][NH:9][C:8]1=[O:17].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Br:1][CH:2]([CH3:6])[C:3]([C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:7][C:8](=[O:17])[NH:9][CH2:10]2)=[O:4]

Participants

5

Reactant 3

HCID 79047Propanoyl bromide, 2-bromo-HCID 6451240Aluminum(III) ChlorideHCID 123607561,2,3,4-Tetrahydroquinazolin-2-one

Product 1

HCID 202016506-(2-Bromopropionyl)-3,4-dihydro-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

2-Bromopropionyl bromide (10.6 g) is added dropwise to a stirring mixture of 3,4-dihydro-2(1H)-quinazolinone (3.2 g) and anhydrous aluminum chloride (7.9 g) in carbon disulfide (60 ml). The reaction mixture is refluxed for four hours, the carbon disulfide decanted and the residue treated with aqueous hydrochloric acid (6N). The acidic residue is poured into ice water, and the precipitate filtered, washed with water and dried, affording the desired product as a solid, which is used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture is refluxed for four hours
  2. customthe carbon disulfide decanted
  3. additionthe residue treated with aqueous hydrochloric acid (6N)
  4. additionThe acidic residue is poured into ice water
  5. filtrationthe precipitate filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-b7997bdaf9ac43c5b3d81ffc9ce96543
Source dataset
uspto-grants-1987_05
Patent number
US04666913

Reaction notes

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