Dimethylformamide → 1-(3-bromopropyl)-3-methyl-2,4(1H)-quinazolinedione

HRID 365099Notes

Reaction equation

HRID 365099 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[NH:7][C:6]1=[O:16].CI.[C:19](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]([CH3:19])[C:6]1=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136872071-(3-bromopropyl)-2,4(1H,3H)-quinazolinedione

Product 1

HCID 136872081-(3-bromopropyl)-3-methyl-2,4(1H)-quinazolinedioneYield 62.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(3-bromopropyl)-2,4(1H,3H)-quinazolinedione (2.83 g), methyl iodide (3 ml), anhydrous potassium carbonate (4.2 g) and N,N-dimethylformamide (25 ml) was stirred for 8 hours at ambient temperature. After the reaction mixture was diluted with cold water, the resultant mixture was extracted twice with chloroform. The chloroform layer was washed with water twice, and with saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resultant oily residue was purified by subjecting to a column chromatography on silica gel (100 g) using chloroform for elution, to give 1-(3-bromopropyl)-3-methyl-2,4(1H,3H)-quinazolinedione (1.85 g) as a crystal.

Workup

  1. extractionthe resultant mixture was extracted twice with chloroform
  2. washThe chloroform layer was washed with water twice
  3. dry with materialwith saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe resultant oily residue was purified
  6. washfor elution

Sources & evidence

ORD record
ord-533da7f8d4e34289b10d5d5aa6b3a3f9
Source dataset
uspto-grants-1986_08
Patent number
US04608375

Reaction notes

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