Benzaldehyde → 1-cyclopropylmethyl-4-phenyl-6-methoxy-3,4-dihydro-2(1H)-quinazolinone

HRID 1395258Notes

Reaction equation

HRID 1395258 reaction equation
[CH:1]1([CH2:4][N:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:6]([NH2:8])=[O:7])[CH2:3][CH2:2]1.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Br.O>C1(C)C=CC=CC=1>[CH:1]1([CH2:4][N:5]2[C:9]3[C:10](=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:8][C:6]2=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 260Hydrogen BromideHCID 962WaterHCID 54367914N-cyclopropylmethyl-N-(p-methoxyphenyl) urea

Product 1

HCID 131890501-cyclopropylmethyl-4-phenyl-6-methoxy-3,4-dihydro-2(1H)-quinazolinoneYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 28.6 g (0.13 mole) of N-cyclopropylmethyl-N-(p-methoxyphenyl) urea in 140 g of toluene were added 13.8 g (0.13 mole) of benzaldehyde and 0.55 g (0.0033 mole) of a 48% hydrobromic acid. The resulting mixture was heated under relux for 10 hours with stirring using a water separator. Thereafter the solvent was removed under reduced pressure and the residue was suspended in a mixture of 80 ml of methanol and 40 g of a 2% hydrochloric acid. The mixture was cooled with ice with stirring. The precipitated crystals were collected by filtration, washed with a mixture of methanol-2% hydrochloric acid (2:1) and then with water, and dried to give 32.0 g (80%) of 1-cyclopropylmethyl-4-phenyl-6-methoxy-3,4-dihydro-2(1H)-quinazolinone, m.p. 133° C.

Workup

  1. temperatureThe resulting mixture was heated under relux for 10 hours
  2. customThereafter the solvent was removed under reduced pressure
  3. additionthe residue was suspended in a mixture of 80 ml of methanol and 40 g of a 2% hydrochloric acid
  4. temperatureThe mixture was cooled with ice
  5. stirringwith stirring
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with a mixture of methanol-2% hydrochloric acid (2:1)
  8. dry with materialwith water, and dried

Sources & evidence

ORD record
ord-5ad3a095f3754450a039c1376cc5837c
Source dataset
uspto-grants-1980_05
Patent number
US04202974

Reaction notes

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