Formic Acid → HCID 12246022, compound

HRID 268529Notes

Reaction equation

HRID 268529 reaction equation
[C:1](OC(=O)C)(=O)C.C(O)=O.[NH2:11][N:12]1[C:21]([OH:28])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([Cl:29])[CH:19]=2)[N:14]=[CH:13]1>C(O)(=O)C>[Cl:29][C:18]1[CH:17]=[CH:16][C:15]([N:14]2[CH:1]=[N:11][N:12]=[CH:13]2)=[C:20]([CH:19]=1)[C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:28]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 1196793-Amino-6-chloro-4-phenyl-3,4-dihydroquinazolin-4-ol

Product 1

HCID 12246022HCID 12246022, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of acetic anhydride (25.3 ml) and 97% formic acid (10.6 ml) is kep at ambient temperature (25°) for 30 minutes, cooled in an ice bath and treated with 3-amino-6-chloro-3,4-dihydro-4-hydroxy-4-phenylquinazoline (12.24 g, 0.0447 mole). The solution is kept at ambient temperature for 18 hours, diluted with acetic acid (25 ml), warmed to the reflux temperature during 1 hour and refluxed for 1.5 hours. The solution is concentrated in vacuo, and the residue is mixed with cold water, made alkaline with sodium hydroxide and extracted with chloroform. The extract is washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue is crystallized from ethylacetate to give 7.76 g of 5-chloro-2-(4H-1,2,4-triazol-4-yl)-benzophenone of melting point 184°-186° C., 0.971 g of melting point 182.5°-184° C., and 0.144 of melting point 181°-182° C.

Workup

  1. customis kep at ambient temperature
  2. custom(25°)
  3. customfor 30 minutes
  4. temperaturecooled in an ice bath
  5. temperaturewarmed to the reflux temperature during 1 hour
  6. temperaturerefluxed for 1.5 hours
  7. concentrationThe solution is concentrated in vacuo
  8. additionthe residue is mixed with cold water
  9. extractionextracted with chloroform
  10. washThe extract is washed with brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe residue is crystallized from ethylacetate

Sources & evidence

ORD record
ord-f34a287504f4477fa97fd29e2df15af9
Source dataset
uspto-grants-1976_03
Patent number
US03947466

Reaction notes

Loading…