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

HRID 979054Notes

Reaction equation

HRID 979054 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[NH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][NH:8][C:7]1=[O:16].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Br:1][CH2:2][C:3]([C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[NH:6][C:7](=[O:16])[NH:8][CH2:9]2)=[O:4]

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 123607561,2,3,4-Tetrahydroquinazolin-2-one

Product 1

HCID 138271626-(Bromoacetyl)-3,4-dihydro-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Bromoacetyl chloride (6.2 g) is added dropwise to a stirring mixture of 3,4-dihydro-2(1H)-quinazolinone (2.6 g) and anhydrous aluminum chloride (6.3 g) in carbon disulfide (60 ml). The reaction mixture is stirred under reflux for 4.5 hours, the carbon disulfide decanted, and the residue treated with HCl (6N). The resulting solid is poured into ice water, 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.

Workup

  1. temperatureunder reflux for 4.5 hours
  2. customthe carbon disulfide decanted
  3. additionthe residue treated with HCl (6N)
  4. additionThe resulting solid is poured into ice water
  5. filtrationfiltered
  6. washthe filtered solid washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-21cb6f0bea814de4b3d7bfa5f078e69d
Source dataset
uspto-grants-1987_05
Patent number
US04666913

Reaction notes

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