Hydrazine hydrate (1:1) → HCID 86711947, compound

HRID 1475255Notes

Reaction equation

HRID 1475255 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15](OCC)=[O:16])=[N:12][CH:11]=2)=[CH:6][CH:5]=1.O.[NH2:23][NH2:24]>CCO>[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15]([NH:23][NH2:24])=[O:16])=[N:12][CH:11]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86711946HCID 86711946, compound

Product 1

HCID 86711947HCID 86711947, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 5-(4-(trifluoromethoxy)phenyl)oxazole-2-carboxylate (6.4 g, 21.2 mmol) in EtOH (30 mL), was added dropwise hydrazine hydrate (6 mL, 84% in H2O) while stifling at RT. The mixture was then stirred for further 16 h at RT and then concentrated under reduced pressure to half volume. Upon addition of H2O (30 mL) a yellow solid precipitated, which was filtered, washed with H2O (3×30 mL) and dried to afford the title compound as a light yellow solid (4.6 g, 75%). MS (ES+) C11H8F3N3O3 requires: 287. found: 288 [M+H]+;

Workup

  1. customwhile stifling at RT
  2. concentrationconcentrated under reduced pressure to half volume
  3. additionUpon addition of H2O (30 mL) a yellow solid
  4. customprecipitated
  5. filtrationwhich was filtered
  6. washwashed with H2O (3×30 mL)
  7. customdried

Sources & evidence

ORD record
ord-2b28bd509ac244cd88035fca062e7f81
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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