Water → HCID 13432848, compound

HRID 1197867Notes

Reaction equation

HRID 1197867 reaction equation
[CH2:1]([C:3]1[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2OC)[C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]=O)=[CH:10][CH:9]=2)=[N:6][N:7]=1)[CH3:2].[OH-].[Na+].[C:27](OCC)(=[O:29])C.O>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([C:3]1[N:4]([C:17]2[CH:18]=[CH:19][C:20]([O:29][CH3:27])=[CH:21][CH:22]=2)[C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH3:15])=[CH:10][CH:9]=2)=[N:6][N:7]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19105235HCID 19105235, compound

Product 1

HCID 13432848HCID 13432848, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
7 °C

Procedure

At ambient temperature, 30 g of the product of Step A were dissolved in 1,200 ml of tetrahydrofuran and the solution was cooled to 7° C. Then, 120 ml of 25% of diethyldihydroaluminate in toluene in 120 ml of tetrahydrofuran were added with stirring for 1 hour at 5°-7° C. After returning to ambient temperature, the mixture was stirred for 2 hours, then cooled again to 7° C. after which 120 ml of sodium hydroxide were added slowly with stirring. Then, the mixture was poured into a mixture of 3,600 ml of ethyl acetate and 600 ml of water. Aftering stirring, the aqueous phase was decanted, and the organic phase was washed with an aqueous solution of sodium hydroxide and then with sodium chloride. Each washing solution was extracted with ethyl acetate and the combined extracts were dried and concentrated to dryness to obtain 23.5 g of crude product which was purified by dissolving it at reflux in 220 ml of ethanol. By filtering hot, washing with refluxing ethanol, concentrating to 110 ml under ambient pressure, cooling, separating, washing with ethanol and drying at 60° C., 10.2 g of 4-[5-ethyl-4-(4-methoxyphenyl)-4H-1,2,4-triazol-3-yl]-N-methyl-benzenamine melting at 198.5° C. were obtained.

Workup

  1. customAfter returning to ambient temperature
  2. stirringthe mixture was stirred for 2 hours
  3. additionwere added slowly
  4. stirringwith stirring
  5. stirringAftering stirring
  6. customthe aqueous phase was decanted
  7. washthe organic phase was washed with an aqueous solution of sodium hydroxide
  8. extractionEach washing solution was extracted with ethyl acetate
  9. customthe combined extracts were dried
  10. concentrationconcentrated to dryness
  11. customto obtain 23.5 g of crude product which
  12. customwas purified
  13. dissolutionby dissolving it
  14. temperatureat reflux in 220 ml of ethanol
  15. filtrationBy filtering hot
  16. washwashing with refluxing ethanol
  17. concentrationconcentrating to 110 ml under ambient pressure
  18. temperaturecooling
  19. customseparating
  20. washwashing with ethanol
  21. customdrying at 60° C.

Sources & evidence

ORD record
ord-f74f2acc7a474fdcb14f85f50eb14e19
Source dataset
uspto-grants-1994_01
Patent number
US05278180

Reaction notes

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