Dicyclohexylcarbodiimide → HCID 178463118, compound

HRID 1709345Notes

Reaction equation

HRID 1709345 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[CH2:23][O:24][CH3:25])(=[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]([CH2:23][O:24][CH3:25])[C:15]=2[CH3:22])[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 14721238HCID 14721238, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 178463118HCID 178463118, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent2×

Procedure

1.12 g (0.01 mol) of 1-ethyl-5-hydroxypyrazole is dissolved in 30 ml of t-amyl alcohol, and then 2.59 g (0.01 mol) of 4-methanesulfonyl-3-methoxymethyl-2-methylbenzoic acid, 2.06 g (0.01 mol) of N,N'-dicyclohexylcarbodiimide and 0.69 g (0.005 mol) of anhydrous potassium carbonate were sequentially added thereto. The mixture was reacted at a temperature of from 80° to 90° C. for 8 hours under stirring. After completion of the reaction, t-amyl alcohol was distilled off under reduced pressure, and 30 ml of water was added to the residue to dissolve the soluble components. The mixture was subjected to filtration to separate out the insolubles. The aqueous solution thus obtained was washed with chloroform, and concentrated hydrochloric acid was added to adjust pH<1. The precipitated oil component was extracted with chloroform. The solvent was distilled off under reduced pressure, and the residue was purified with silica gel column chromatography (eluent: ethyl acetate/ethanol=9/1) to obtain 2.3 g of the desired product. (Yield: 66%, melting point: 116°-118° C.)

Workup

  1. customThe mixture was reacted at a temperature of from 80° to 90° C. for 8 hours
  2. distillationwas distilled off under reduced pressure, and 30 ml of water
  3. additionwas added to the residue
  4. dissolutionto dissolve the soluble components
  5. filtrationThe mixture was subjected to filtration
  6. customto separate out the insolubles
  7. customThe aqueous solution thus obtained
  8. washwas washed with chloroform, and concentrated hydrochloric acid
  9. additionwas added
  10. extractionThe precipitated oil component was extracted with chloroform
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue was purified with silica gel column chromatography (eluent: ethyl acetate/ethanol=9/1)

Sources & evidence

ORD record
ord-89a2568f078949d4a98ad827635d2315
Source dataset
uspto-grants-1990_08
Patent number
US04948887

Reaction notes

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