Hydrochloric Acid → 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 394096Notes

Reaction equation

HRID 394096 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18](OC)=[O:19])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:30])[N:13]2[C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.C(OCC)(=O)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18][OH:19])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:30])[N:13]2[C:22]1[C:23]([Cl:29])=[CH:24][CH:25]=[CH:26][C:27]=1[Cl:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride3×HCID 22648138Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate2×

Product 1

HCID 226479725-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

To a stirred solution of methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (INTERMEDIATE 32) (8.23 g) in THF (140 mL) was added lithium aluminum hydride (14 mL of a 1.0M solution in THF) and the mixture was let stir 1.5 h. More lithium aluminum hydride (4.5 mL of a 1.0M solution in THF) was added and the mixture was stirred overnight. Another portion of lithium aluminum hydride (4.5 mL of a 1.0M solution in THF) was added and stirred 4 h. The reaction was carefully poured into a flask containing 1N aqueous HCl (500 mL) and stirred. To the mixture was added ethyl acetate (500 mL) and the layers were mixed, then separated. The organic layer was washed with brine (300 mL), dried over anhydrous MgSO4, filtered and concentrated. The resulting solid was triturated with hexanes, then CH2Cl2 to give the 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one compound.

Workup

  1. stirringthe mixture was stirred overnight
  2. stirringstirred 4 h
  3. additionThe reaction was carefully poured into a flask
  4. stirringstirred
  5. additionthe layers were mixed
  6. customseparated
  7. washThe organic layer was washed with brine (300 mL)
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting solid was triturated with hexanes

Sources & evidence

ORD record
ord-fdf06b08eff84560976b95b7e7912b7f
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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