Hydrazine hydrate (1:1) → HCID 66577662, compound

HRID 1183302Notes

Reaction equation

HRID 1183302 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[C:14]([OH:16])=O)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:30][NH2:31]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[C:14]([NH:30][NH2:31])=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-CarbonyldiimidazoleHCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 66577662HCID 66577662, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (0.061 g, 2.16 mmol) was dissolved in THF (5 mL) then 1,1′-carbonyldiimidazole (0.390 g, 2.38 mmol) was added and the reaction was heated to 70° C. for 40 minutes. The reaction was then cooled to 0° C. and hydrazine monohydrate (0.220 mL, 4.32 mmol) was added. The reaction was then allowed to slowly warm to room temperature and stirred overnight. Standard aqueous workup afforded the title compound, which was brought to the next step without further purification.

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. temperatureto slowly warm to room temperature

Sources & evidence

ORD record
ord-3023208586b34048b944b0d511461664
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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