Potassium Hydroxide → HCID 135748512, compound

HRID 437063Notes

Reaction equation

HRID 437063 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].[C:6]([C:8]1[C:9]([C:22]2[N:23]([CH3:30])[C:24]([N+:27]([O-:29])=[O:28])=[CH:25][N:26]=2)=[N:10][N:11]([CH3:21])[C:12]=1[NH:13][C:14](=[O:20])[C:15](OCC)=[O:16])#[N:7]>CO>[C:6]([C:8]1[C:9]([C:22]2[N:23]([CH3:30])[C:24]([N+:27]([O-:29])=[O:28])=[CH:25][N:26]=2)=[N:10][N:11]([CH3:21])[C:12]=1[NH:13][C:14]([C:15]([NH:2][OH:3])=[O:16])=[O:20])#[N:7]

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 443297Hydroxyamine hydrochloride2×HCID 57421991HCID 57421991, compound

Product 1

HCID 135748512HCID 135748512, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Separate solutions were prepared of 0.94 g. of hydroxylamine hydrochloride in 10 ml. of methanol, and 0.728 g. of potassium hydroxide in 5 ml. of methanol at the boiling point of methanol. Both solutions were then cooled to about 30°-40° C., and the potassium hydroxide solution was added with shaking to the hydroxylamine hydrochloride solution. After the addition, the flask containing the mixture was flushed with nitrogen so that the mixture was maintained in a nitrogen atmosphere while being cooled in an ice bath for about 5 minutes to insure complete precipitation of the potassium chloride. The potassium chloride was filtered off and the filtrate diluted with about 50 ml. of methanol. To this methanolic solution, there was then added 2.3 g. (0.0067 mole) of N-[4-cyano-1-methyl-3-(1-methyl-5-nitroimidazol-2-yl)pyrazol-5-yl]oxamic acid, ethyl ester, and the mixture was stirred for about 3 hours at ambient room temperature. A precipitate formed which was filtered off. The solid so collected was refluxed in methanol and the solid which did not dissolve was collected on a filter. The solid weighed about 0.3 g. and had a melting point of about 179°-180° C. The solid was identified by NMR spectrum and elemental analyses as N-[4-cyano-1-methyl-3-(1-methyl-5-nitroimidazol-2-yl)pyrazol-5-yl]-N'-hydroxyoxamide.

Workup

  1. customSeparate solutions
  2. customwere prepared of 0.94 g
  3. temperatureBoth solutions were then cooled to about 30°-40° C.
  4. additionAfter the addition
  5. additionthe flask containing the mixture
  6. customwas flushed with nitrogen so that the mixture
  7. temperaturewas maintained in a nitrogen atmosphere
  8. temperaturewhile being cooled in an ice bath for about 5 minutes
  9. customprecipitation of the potassium chloride
  10. filtrationThe potassium chloride was filtered off
  11. additionthe filtrate diluted with about 50 ml
  12. additionTo this methanolic solution, there was then added 2.3 g
  13. customA precipitate formed which
  14. filtrationwas filtered off
  15. customThe solid so collected
  16. temperaturewas refluxed in methanol
  17. dissolutionthe solid which did not dissolve
  18. customwas collected on a filter

Sources & evidence

ORD record
ord-c0a7b683d66049aebd46a58422126aa8
Source dataset
uspto-grants-1977_06
Patent number
US04029671

Reaction notes

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