1,1'-Carbonyldiimidazole → 3,4-Dihydro-3-methyl-2(1H)-quinazolinone

HRID 1607988

Reaction equation

HRID 1607988 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].CN[CH2:15][C:16]1C=CC=C[C:17]=1N>C1COCC1>[CH3:9][N:8]1[CH2:12][C:11]2[C:7](=[CH:6][CH:15]=[CH:16][CH:17]=2)[NH:3][C:1]1=[O:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 118154102-[(Methylamino)methyl]aniline

Product 1

HCID 38465583,4-Dihydro-3-methyl-2(1H)-quinazolinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-Carbonyl-diimidazole (16.7 g) is added to a solution of 2-(methylaminomethyl)-aniline (11.2 g) in anhydrous THF (30 ml) under nitrogen. The reaction mixture is refluxed for about 24 hours, stirred for 48 hours at RT and filtered. The filtered precipitate is suspended in 2N HCl for about 40 minutes, filtered, and the filtered solid washed with water and air dried, affording the desired product, M.P. 202-206.5 C., used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture is refluxed for about 24 hours
  2. filtrationfiltered
  3. waitThe filtered precipitate is suspended in 2N HCl for about 40 minutes
  4. filtrationfiltered
  5. washthe filtered solid washed with water and air
  6. customdried

Sources & evidence

ORD record
ord-fa30c02c503e45eda724856b9cdf3a4e
Source dataset
uspto-grants-1989_09
Patent number
US04868300

Linked notes

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