Heptane → 5-Methyl-3-phenyl-4-isoxazolecarbohydrazide

HRID 1983080

Reaction equation

HRID 1983080 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:29][NH2:30].CCCCCCC>C1COCC1>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([NH:29][NH2:30])=[O:15]

Participants

6

Reactant 4

HCID 8900HeptaneHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 7279245-Methyl-3-phenyl-4-isoxazolecarbohydrazideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (5.00 g, 24.6 mmol) in THF (50 mL) was added in one portion 1,1′-carbonyl-diimidazole (4.39 g, 27.1 mmol). After stirring for 15 min at ambient temperature the solution was warmed to 70° C. and stirred for 30 min at this temperature. After the solution was cooled to 0° C. hydrazine monohydrate (2.4 mL, 49.0 mmol) was added over a period of 2 min while the temperature raised to 15° C. The resulting suspension was stirred for 30 min at 0° C. After addition of 20 mL heptane the suspension was stirred for 15 min at 0° C. and filtered off. Washing with water and drying afforded the title compound (4.52 g, 85%) as a white solid. MS: m/e=218.2 [M+H]+.

Workup

  1. temperaturewas warmed to 70° C.
  2. stirringstirred for 30 min at this temperature
  3. additionwas added over a period of 2 min while the temperature
  4. temperatureraised to 15° C
  5. stirringThe resulting suspension was stirred for 30 min at 0° C
  6. stirringwas stirred for 15 min at 0° C.
  7. filtrationfiltered off
  8. washWashing with water
  9. customdrying

Sources & evidence

ORD record
ord-b6859324313a427eba4754a44a3585f4
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Linked notes

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