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

HRID 1871271

Reaction equation

HRID 1871271 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 mnl). 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 mnl)
  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-6bfec79fd36f4943baf38a027481c3b2
Source dataset
uspto-grants-2000_08
Patent number
US06103731

Linked notes

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