Hydrochloric Acid → 1,2-Oxazole-3-carbohydrazide

HRID 1889029Notes

Reaction equation

HRID 1889029 reaction equation
C(OC([NH:8][NH:9][C:10]([C:12]1[CH:16]=[CH:15][O:14][N:13]=1)=[O:11])=O)(C)(C)C.Cl.O1CCOCC1>>[O:14]1[CH:15]=[CH:16][C:12]([C:10]([NH:9][NH2:8])=[O:11])=[N:13]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66598851HCID 66598851, compound

Product 1

HCID 543385531,2-Oxazole-3-carbohydrazide

Procedure

Solid t-butyl-2-(3-isoxazolylcarbonyl)hydrazinecarboxylate (I88) (510 mg, 1.639 mmol) was treated with a solution of hydrochloric acid (4 M) in dioxane (8.19 ml, 32.8 mmol) and stirred under argon at RT for 6 hr. The solvent was evaporated in vacuo and the residue dissolved in methanol (˜10 ml), added to a 10 g SCX column and eluted with Dichloromethane (˜50 ml), methanol (˜50 ml) and a solution of ammonia (2 M) in methanol (˜100 ml). The basic fractions were combined and evaporated in vacuo to afford the free base as yellow dendriform crystals in 211.0 mg.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in methanol (˜10 ml)
  3. additionadded to a 10 g SCX column
  4. washeluted with Dichloromethane (˜50 ml), methanol (˜50 ml)
  5. customevaporated in vacuo
  6. customto afford the free base as yellow dendriform crystals in 211.0 mg

Sources & evidence

ORD record
ord-1cb5036cc1064d2c8cace238989d2266
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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