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

HRID 1164796Notes

Reaction equation

HRID 1164796 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-1f7cc818aa1949aa83a60cf2ab70a941
Source dataset
uspto-grants-1990_03
Patent number
US04906630

Reaction notes

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