Dicyclohexylcarbodiimide → HCID 178428866, compound

HRID 50554Notes

Reaction equation

HRID 50554 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]1([N:21]2[C:25]([OH:26])=[CH:24][CH:23]=[N:22]2)[CH2:20][CH2:19][CH2:18][CH2:17]1.[CH3:27][C:28]1[C:36]([C:37]2[CH2:41][CH2:40][O:39][N:38]=2)=[C:35]([S:42]([CH3:45])(=[O:44])=[O:43])[CH:34]=[CH:33][C:29]=1[C:30](O)=[O:31].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:27][C:28]1[C:36]([C:37]2[CH2:41][CH2:40][O:39][N:38]=2)=[C:35]([S:42]([CH3:45])(=[O:44])=[O:43])[CH:34]=[CH:33][C:29]=1[C:30]([C:24]1[CH:23]=[N:22][N:21]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[C:25]=1[OH:26])=[O:31]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 154774763-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)benzoic acidHCID 178516540HCID 178516540, compound

Product 1

HCID 178428866HCID 178428866, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.9 g (9.4 mmol) of dicyclohexylcarbodiimide and 1.3 g (8.8 mmol) of 1-cyclopentyl-5-hydroxy-1H-pyrazole were added to a solution of 2.5 g (8.8 mmol) of 2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid in 100 ml of dioxane, and the mixture was stirred at room temperature for 12 hours. Solid components were then filtered off and the filtrate was admixed with 1.5 g (10 mmol) of potassium carbonate and refluxed for 4 hours. The solvent was removed, the residue was then taken up in water and the mixture was washed with ethyl acetate, and then adjusted to pH 3 using 10% strength hydrochloric acid and extracted with methylene chloride. The solvent of the resulting organic phase was distilled off, the residue was taken up in 300 ml of aqueous potassium carbonate solution, insoluble components were filtered off, the pH was adjusted to 3 using 10% strength hydrochloric acid and the resulting precipitate was separated off and dried. Yield: 1.5 g (42% of theory) of 4-[2-methyl-3-(4,5-dihydro-isoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-cyclopentyl-5-hydroxy-1H-pyrazole

Workup

  1. filtrationSolid components were then filtered off
  2. temperaturerefluxed for 4 hours
  3. customThe solvent was removed
  4. washthe mixture was washed with ethyl acetate
  5. extractionextracted with methylene chloride
  6. distillationThe solvent of the resulting organic phase was distilled off
  7. filtrationinsoluble components were filtered off
  8. customthe resulting precipitate was separated off
  9. customdried

Sources & evidence

ORD record
ord-75fd9d926d8d4e8f87e2c8d8eefe190c
Source dataset
uspto-grants-2004_03
Patent number
US06713436B1

Reaction notes

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