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

HRID 979059Notes

Reaction equation

HRID 979059 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].[CH3:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10](=[O:18])[NH:9]1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Br:1][CH:2]([CH3:6])[C:3]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:18])[NH:9][CH:8]2[CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 79047Propanoyl bromide, 2-bromo-HCID 6451240Aluminum(III) ChlorideHCID 123607574-Methyl-3,4-dihydro-1H-quinazolin-2-one

Product 1

HCID 138271686-(2-Bromopropionyl)-3,4-dihydro-4-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

2-Bromopropionyl bromide (16 g) is added dropwise to a mixture of 3,4-dihydro-4-methyl-2(1H)-quinazolinone (6.1 g) and anhydrous aluminum chloride (12.5 g) in carbon disulfide (110 ml). The reaction mixture is refluxed overnight under nitrogen, the carbon disulfide is decanted and the residue treated with hydrochloric acid (6N). The acidic residue is treated with ethyl acetate and the layers separated. The aqueous layer is extracted with ethyl acetate and the combined organic extracts washed with sat'd. aqueous sodium bicarbonate and water and dried. The organic layer is filtered and the filtrate stripped in vacuo, affording an oil which crystallizes in vacuo, M.P. 153°-156° C.

Workup

  1. temperatureThe reaction mixture is refluxed overnight under nitrogen
  2. customthe carbon disulfide is decanted
  3. additionthe residue treated with hydrochloric acid (6N)
  4. additionThe acidic residue is treated with ethyl acetate
  5. customthe layers separated
  6. extractionThe aqueous layer is extracted with ethyl acetate
  7. washthe combined organic extracts washed with sat'd
  8. dry with materialaqueous sodium bicarbonate and water and dried
  9. filtrationThe organic layer is filtered
  10. customaffording an oil which
  11. customcrystallizes in vacuo, M.P. 153°-156° C.

Sources & evidence

ORD record
ord-55506794ce8548a9b4a2877889461cfa
Source dataset
uspto-grants-1987_05
Patent number
US04666913

Reaction notes

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