Water → HCID 15682543, compound

HRID 1590000Notes

Reaction equation

HRID 1590000 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH2:6]([C:9]1[O:13][N:12]=[C:11]([C:14](Cl)=[O:15])[CH:10]=1)[CH2:7][CH3:8].O>ClCCl>[C:1]([NH:5][C:14]([C:11]1[CH:10]=[C:9]([CH2:6][CH2:7][CH3:8])[O:13][N:12]=1)=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 156825425-Propyl-3-isoxazolecarbonyl chloride

Product 1

HCID 15682543HCID 15682543, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 5° C., 9.3 g (126.8 mmol) of tert-butylamine in 20 ml of dichloromethane was dripped into 10.0 g (57.6 mmol) of 5-n-propyl-isoxazole-3-carboxylic chloride in 250 ml of anhydrous dichloromethane. The mixture was stirred for 12 hours at room temperature, 200 ml of water was added, the phases were separated, the organic phase was washed once with 150 ml of saturated sodium bicarbonate solution and once with 150 ml of saturated sodium chloride solution, followed by drying over magnesium sulfate and stripping off the solvent under reduced pressure. There was obtained 11.5 g (95%) of 5-n-propylisoxazole-3-carboxylic acid-tert-butylamide as a solid of melting point 34°-37° C.

Workup

  1. customAt 5° C.
  2. customthe phases were separated
  3. washthe organic phase was washed once with 150 ml of saturated sodium bicarbonate solution and once with 150 ml of saturated sodium chloride solution
  4. dry with materialby drying over magnesium sulfate

Sources & evidence

ORD record
ord-f6cad92dab894c4e97171b65562e5274
Source dataset
uspto-grants-1993_04
Patent number
US05201932

Reaction notes

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