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

HRID 34902
Notes
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Reaction equation

HRID 34902 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 (71.02 g) is added dropwise to a stirred mixture of 3,4-dihydro-3-methyl-2(1H)quinazolinone (26.75 g) and anhydrous aluminum chloride (54.98 g) in carbon disulfide (350 ml). The reaction mixture is stirred under reflux for 5 hrs., the carbon disulfide decanted, and the residue treated with HCl (6N). The resulting solid is filtered, and washed with water and dried in vacuo to obtain 6-(2-bromopropionyl)-3,4,dihydro-3-methyl-2(1H)-quinazolinone which is used in the next step.

Workup

  1. temperatureunder reflux for 5 hrs
  2. custom, the carbon disulfide decanted
  3. additionthe residue treated with HCl (6N)
  4. filtrationThe resulting solid is filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b3ac7eeee5c14cba98b5023f718d0974
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04764512

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes