Pyridine → HCID 21494726, compound

HRID 1731101Notes

Reaction equation

HRID 1731101 reaction equation
[NH2:1][N:2]1[C:11]([OH:18])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:19])[CH:9]=2)[N:4]=[CH:3]1.N1C=CC=CC=1.[C:26]1(=[O:41])[N:30]([CH2:31][CH2:32][C:33](Cl)=O)[C:29](=[O:36])[C:28]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:27]12.C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:19][C:8]1[CH:7]=[CH:6][C:5]([N:4]2[CH:3]=[N:2][N:1]=[C:33]2[CH2:32][CH2:31][N:30]2[C:29](=[O:36])[C:28]3=[CH:37][CH:38]=[CH:39][CH:40]=[C:27]3[C:26]2=[O:41])=[C:10]([CH:9]=1)[C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 869661,3-dihydro-1,3-dioxo-2H-isoindole-2-propionyl chlorideHCID 1196793-Amino-6-chloro-4-phenyl-3,4-dihydroquinazolin-4-olHCID 516892Sodium Bicarbonate

Product 1

HCID 21494726HCID 21494726, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred mixture of 3-amino-6-chloro-3,4-dihydro-4-hydroxy-4-phenylquinazoline (2.74 g. 0.01 mole) in dry tetrahydrofuran (150 ml.) is cooled in an ice bath, under nitrogen, and treated with dry pyridine (1.77 ml., 0.022 mole). This mixture is then treated dropwise, during 1 hour with a solution of β-phthalimidopropionyl chloride (5.23 g., 0.022 mole) in tetrahydrofuran (25 ml.). The mixture is kept in the ice bath for 1 hour and at ambient temperature for 4 hours. It is then poured into cold, dilute aqueous sodium bicarbonate and extracted with chloroform. The extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is mixed with toluene (165 ml.), treated with trifluoroacetic acid (0.732 ml.) and warmed, under nitrogen at 100°-110° C. for 1.5 hours. The mixture is concentrated in vacuo and the residue mixed with cold water and extracted with chloroform. The extract is washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on silica gel (300 g) with 1.5% methanol-98.5% chloroform. The product thus obtained is crystallized to give 5-chloro-2-[3-(2-phthalimidoethyl)-4H-1,2,4-triazol-4-yl]benzophenone.

Workup

  1. temperatureis cooled in an ice bath, under nitrogen
  2. extractionextracted with chloroform
  3. washThe extract is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue is mixed with toluene (165 ml.)
  7. additiontreated with trifluoroacetic acid (0.732 ml.)
  8. temperaturewarmed, under nitrogen at 100°-110° C. for 1.5 hours
  9. concentrationThe mixture is concentrated in vacuo
  10. additionthe residue mixed with cold water
  11. extractionextracted with chloroform
  12. washThe extract is washed with brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationconcentrated
  15. customThe residue is chromatographed on silica gel (300 g) with 1.5% methanol-98.5% chloroform
  16. customThe product thus obtained
  17. customis crystallized

Sources & evidence

ORD record
ord-f9b994b2990346ad914649f5670b8862
Source dataset
uspto-grants-1976_11
Patent number
US03994940

Reaction notes

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