Dicyclohexylcarbodiimide → HCID 178463120, compound

HRID 1682158Notes

Reaction equation

HRID 1682158 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[CH:6][CH:5]=[N:4]1)[CH3:2].[CH3:9][S:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[C:15]([CH3:22])[C:14]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:12])=[O:11].C1(N=C=NC2CCCCC2)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)(CC)(C)C>[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([S:10]([CH3:9])(=[O:12])=[O:11])=[C:14]([C:23]([O:25][CH3:26])=[O:24])[C:15]=2[CH3:22])[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 156236574-Methanesulfonyl-3-methoxycarbonyl-2-methylbenzoic acidHCID 178418331HCID 178418331, compound

Product 1

HCID 178463120HCID 178463120, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent2×

Procedure

1.12 g (0.01 mol) of 1-ethyl-5-hydroxypyrazole was dissolved in 30 ml of t-amyl alcohol, and 2.72 g (0.01 mol) of 4-methanesulfonyl-3-methoxycarbonyl-2-methylbenzoic acid, 2.27 g (0.011 mol) of N,N'-dicyclohexylcarbodiimide and 0.76 g (0.0055 mol) of anhydrous potassium carbonate were sequentially added thereto. The mixture was reacted at 80° C. for 6 hours under stirring. After completion of the reaction, t-amyl alcohol was distilled off under reduced pressure, and then water was added to the residue to dissolve the soluble component. The mixture was subjected to filtration to separate out the insolubles. The aqueous solution thus obtained was washed twice with chloroform, and then concentrated hydrochloric acid was added to adjust pH<1. The precipitated oil component was extracted with chloroform. The chloroform layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue thus obtained was recrystallized from water/ethanol to obtain 2.26 g of the desired product. (Yield: 62%, melting point: 150°-152° C.)

Workup

  1. customThe mixture was reacted at 80° C. for 6 hours
  2. distillationwas distilled off under reduced pressure
  3. additionwater was added to the residue
  4. dissolutionto dissolve the soluble component
  5. filtrationThe mixture was subjected to filtration
  6. customto separate out the insolubles
  7. customThe aqueous solution thus obtained
  8. washwas washed twice with chloroform
  9. additionconcentrated hydrochloric acid was added
  10. extractionThe precipitated oil component was extracted with chloroform
  11. washThe chloroform layer was washed sequentially with water
  12. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  13. distillationThen, the solvent was distilled off under reduced pressure
  14. customthe residue thus obtained
  15. customwas recrystallized from water/ethanol

Sources & evidence

ORD record
ord-b03e6b725bb5445d890de8631c03b832
Source dataset
uspto-grants-1992_12
Patent number
US05175299

Reaction notes

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