Formamidine acetate → 5,7-dibenzyloxy-3,4-dihydroquinazolin-4-one

HRID 1826255Notes

Reaction equation

HRID 1826255 reaction equation
N[C:2]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[C:8]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]=1[C:4](OC)=[O:5].C(O)(=O)C.[CH:32]([NH2:34])=[NH:33]>COCCO>[CH2:21]([O:20][C:8]1[CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:33][CH:32]=[N:34]2)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 11974450HCID 11974450, compound

Product 1

HCID 1355106905,7-dibenzyloxy-3,4-dihydroquinazolin-4-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of methyl 2-amino-4,6-dibenzyloxybenzoate (7.7 g), formamidine acetate (7.2 g) and 2-methoxyethanol (100 ml) was stirred and heated to reflux until all of the starting material had reacted. The mixture was evaporated and the residue was triturated under water (60 ml). The resultant solid was isolated, washed with water and dried under vacuum to give 5,7-dibenzyloxy-3,4-dihydroquinazolin-4-one (6.8 g); NMR Spectrum: (DMSOd6) 5.24 (s, 4H), 6.75 (s, 1H), 6.8 (s, 1H), 7.3–7.7 (m, 10H), 7.95 (s, 1H), 11.75 (br s, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux until all of the starting material
  3. customhad reacted
  4. customThe mixture was evaporated
  5. customthe residue was triturated under water (60 ml)
  6. customThe resultant solid was isolated
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-77ae406fc05049a7a0cf73faa5b87621
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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