Acetohydrazide → HCID 22768926, compound

HRID 1764633Notes

Reaction equation

HRID 1764633 reaction equation
[C:1]([NH:4][NH2:5])(=O)[CH3:2].Cl[C:7]1[N:12]=[N:11][C:10]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)=[C:9]([CH3:21])[CH:8]=1>C(O)CCC>[CH3:2][C:1]1[N:12]2[N:11]=[C:10]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)[C:9]([CH3:21])=[CH:8][C:7]2=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 13424594HCID 13424594, compound

Product 1

HCID 22768926HCID 22768926, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A 1.48 g. portion of acetic acid hydrazide is dissolved in 50 ml. of butyl alcohol with heating, then 4.58 g. of p-(6-chloro-4-methyl-3-pyridazinyl)benzonitrile (prepared as in Example 1) is added and complete solution occurs after heating for an additional 10 minutes. The solution is then heated at reflux for 18 hours. The reaction mixture is concentrated to afford 5.8 g. of orange solid which is washed with petroleum ether. This product is dissolved in 1:1 ethyl alcohol/acetone and is filtered through a pad of silica gel. The filter is washed copiously with acetone and the combined filtrates are concentrated to a yellow solid. The solid is dissolved in 100 ml. of acetone and the solution is cooled in dry ice-acetone to afford a tan solid which is collected by filtration, washed copiously with petroleum ether and air dried. This product is dissolved in methyl alcohol, is treated with activated charcoal and is filtered. The filtrate is used to recrystallize 1.06 g. of yellowish crystals. A 500 mg. portion of the above is recrystallized twice from methanol and the resultant product is dried in vacuo to give the product of the example, m.p. 242°-244° C.

Workup

  1. temperatureafter heating for an additional 10 minutes
  2. temperatureThe solution is then heated
  3. temperatureat reflux for 18 hours
  4. concentrationThe reaction mixture is concentrated
  5. customto afford 5.8 g
  6. washof orange solid which is washed with petroleum ether
  7. dissolutionThis product is dissolved in 1:1 ethyl alcohol/acetone
  8. filtrationis filtered through a pad of silica gel
  9. washThe filter is washed copiously with acetone
  10. concentrationthe combined filtrates are concentrated to a yellow solid
  11. dissolutionThe solid is dissolved in 100 ml
  12. temperatureof acetone and the solution is cooled in dry ice-acetone
  13. customto afford a tan solid which
  14. filtrationis collected by filtration
  15. washwashed copiously with petroleum ether and air
  16. customdried
  17. dissolutionThis product is dissolved in methyl alcohol
  18. additionis treated with activated charcoal
  19. filtrationis filtered
  20. customto recrystallize 1.06 g
  21. customportion of the above is recrystallized twice from methanol
  22. dry with materialthe resultant product is dried in vacuo
  23. customto give the product of the example, m.p. 242°-244° C.

Sources & evidence

ORD record
ord-8e6db10da0fe4c049fb5dccef1286e71
Source dataset
uspto-grants-1978_09
Patent number
US04117130

Reaction notes

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