HCID 86736366, compound → HCID 21325712, compound

HRID 614050Notes

Reaction equation

HRID 614050 reaction equation
[C:1]1(=[O:37])[N:5]([CH2:6][C:7]([NH:9][CH2:10][C:11]([NH:13][N:14]2[C:23]([OH:30])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Cl:31])[CH:21]=3)[N:16]=[CH:15]2)=O)=[O:8])[C:4](=[O:32])[C:3]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:2]12>C(O)(=O)C>[Cl:31][C:20]1[CH:19]=[CH:18][C:17]([N:16]2[CH:15]=[N:14][N:13]=[C:11]2[CH2:10][NH:9][C:7](=[O:8])[CH2:6][N:5]2[C:4](=[O:32])[C:3]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:2]3[C:1]2=[O:37])=[C:22]([CH:21]=1)[C:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:30]

Participants

3

Reactant 1

HCID 86736366HCID 86736366, compound

Product 1

HCID 21325712HCID 21325712, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-[Nα -(2-phthalimidoacetyl)-glycylamino]-4-hydroxy-4-phenyl-6-chloro-3,4-dihydroquinazoline (0.7 g) in acetic acid (5 ml) is refluxed with heating for 2.5 hours. The reaction mixture is evaporated under reduced pressure, and the residue is dissolved in ethyl acetate. The ethyl acetate layer is washed with saturated aqueous sodium bicarbonate and water in order, dried over sodium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is chromatographed on a column of silica gel, which is eluted with ethyl acetate-methanol (20:1) to give 5-chloro-2-[3-(2-phthalimidoacetamidomethyl)-4H-1,2,4-triazol-4-yl]benzophenone as crystals melting at 214° to 215° C.

Workup

  1. temperaturewith heating for 2.5 hours
  2. customThe reaction mixture is evaporated under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThe ethyl acetate layer is washed with saturated aqueous sodium bicarbonate and water in order
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is chromatographed on a column of silica gel, which
  9. washis eluted with ethyl acetate-methanol (20:1)

Sources & evidence

ORD record
ord-90ae0c3e60ac42ab87caaa01606552fd
Source dataset
uspto-grants-1979_03
Patent number
US04143048

Reaction notes

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