Formaldehyde → 3-(4-Methoxyphenyl)-5,6-dihydroimidazo[1,5-c]quinazoline

HRID 378901

Reaction equation

HRID 378901 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH2:20])[N:13]=2)=[CH:5][CH:4]=1.[CH2:21]=O>C(O)(=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:13]3[CH2:21][NH:20][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[C:12]3=[CH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 178488922HCID 178488922, compound

Product 1

HCID 154787163-(4-Methoxyphenyl)-5,6-dihydroimidazo[1,5-c]quinazoline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Methoxyphenyl)-4-(2-aminophenyl)imidazole (5 g) is dissolved in acetic acid (20 ml) and formaldehyde (37% in water, 1.53 ml) is added. The reaction is stirred for 2 min., diluted with ethyl acetate (100 ml), and extracted with 5%HCl (250 ml). The aqueous layer is basified with K2CO3, then extracted with ethyl acetate. The organic layer is evaporated under reduced pressure and the residue is recrystallized from dichloromethane to afford 3-(4-methoxyphenyl)-5,6-dihydroimidazo[1,5-c]quinazoline (3 g) as a light brown solid. m.p. 190-191° C.

Workup

  1. extractionextracted with 5%HCl (250 ml)
  2. extractionextracted with ethyl acetate
  3. customThe organic layer is evaporated under reduced pressure
  4. customthe residue is recrystallized from dichloromethane

Sources & evidence

ORD record
ord-2057ce4073d3435eb24c3fa45fe7efb8
Source dataset
uspto-grants-2001_10
Patent number
US06297252B1

Linked notes

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