Sodium Hydroxide → HCID 13686018, compound

HRID 1380522Notes

Reaction equation

HRID 1380522 reaction equation
Cl.Cl.[O:3]([CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[NH:21][C:22]([NH2:25])=[N:23][N:24]=2)[CH2:16][CH2:15]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].[Br:28][CH:29]([CH:32]=O)[CH:30]=O>O>[Br:28][C:29]1[CH:30]=[N:25][C:22]2[N:23]([N:24]=[C:20]([N:17]3[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][CH2:11][CH2:10][O:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:19][CH2:18]3)[N:21]=2)[CH:32]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 749452-BromopropanedialHCID 178478676HCID 178478676, compound

Product 1

HCID 13686018HCID 13686018, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 10.0 g (0.03 mole) amount of 5-[4-(4-phenoxybutyl)-1-piperazinyl]-4H-1,2,4-triazol-3-amine, dihydrochloride was partially dissolved in 20 ml of water, then 5N sodium hydroxide was added to adjust the pH to just greater than pH 7, resulting in formation of a solid. The solid was collected by filtration and washed with water. The colorless crystals, were transfered into a 125 ml round bottom flask and dissolved in 50 ml of ethanol. Then 7.5 g (0.05 moles) of bromomalonaldehyde was added and the mixture was heated at reflux for 7 hours. The reaction mixture was cooled and filtered. The filter was washed with ethanol/ether, then ether. The filtrate was evaporated in vacuo, combined with the filter cake, extracted with hot chloroform and filtered. The filtrate was passed through a pad of magnesium silicate and the pad was washed with chloroform. The combined chloroform filtrate and wash was evaporated to a syrup. Crystallization from ethanol gave 2.2 g of the desired product as pale yellow crystals, mp 122°-123° C.

Workup

  1. customresulting in formation of a solid
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customThe colorless crystals, were transfered into a 125 ml round bottom flask
  5. dissolutiondissolved in 50 ml of ethanol
  6. temperaturethe mixture was heated
  7. temperatureat reflux for 7 hours
  8. temperatureThe reaction mixture was cooled
  9. filtrationfiltered
  10. washThe filter was washed with ethanol/ether
  11. customThe filtrate was evaporated in vacuo
  12. extractionextracted with hot chloroform
  13. filtrationfiltered
  14. washthe pad was washed with chloroform
  15. washThe combined chloroform filtrate and wash
  16. customwas evaporated to a syrup
  17. customCrystallization from ethanol

Sources & evidence

ORD record
ord-8cc5f6b02aca4384967b128b94e47040
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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