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

HRID 979056

Reaction equation

HRID 979056 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:17].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Br:1][CH2:2][C:3]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:17])[N:7]([CH3:6])[CH2:16]2)=[O:4]

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 38465583,4-Dihydro-3-methyl-2(1H)-quinazolinoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 138271656-(Bromoacetyl)-3,4-dihydro-3-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Bromoacetyl chloride (4.8 g) is added dropwise to a stirring solution 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 and the carbon disulfide decanted. The residue is treated with hydrochloric acid (6N) and the acidic residue poured into ice water, stirred and filtered. The filtered solid is washed with water and dried in vacuo, affording the desired product, which is used in the next step without further purification, M.P. 190°-200° C. (dec).

Workup

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

Sources & evidence

ORD record
ord-98d69d64549a406cbdea5fa4bc3c32bb
Source dataset
uspto-grants-1987_05
Patent number
US04666913

Linked notes

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