Dicyclohexylcarbodiimide → HCID 178463134, compound

HRID 2379376Notes

Reaction equation

HRID 2379376 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:9]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(=O)([O-])[O-].[K+].[K+].[CH2:26]([N:28]1[C:32]([OH:33])=[CH:31][CH:30]=[N:29]1)[CH3:27].C1(N=C=NC2CCCCC2)CCCCC1>C(O)(CC)(C)C>[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:9]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:8]=[CH:7][C:3]=1[C:4]([C:31]1[CH:30]=[N:29][N:28]([CH2:26][CH3:27])[C:32]=1[OH:33])=[O:6]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 14851251HCID 14851251, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 178463134HCID 178463134, compound

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

1.2 g of the crude product of 2-chloro-4-methanesulfonyl-3-(2-methoxy)ethoxybenzoic acid, 0.3 g of potassium carbonate, 0.45 g of 1-ethyl-5-hydroxypyrazole and 0.77 g of N,N'-dicyclohexyl carbodiimide were put into 40 ml of t-amyl alcohol, and the mixture was stirred under heating at a temperature of from 80° to 90° C. for from 4 to 5 hours. The solvent was distilled off, and a dilute potassium carbonate aqueous solution was added to the residue. The mixture was washed with chloroform. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with chloroform. The extract was dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain a crude product of the above identified compound. The crude product was recrystallized from ethanol to obtain 0.3 g of the desired product. Melting point: 159°-160° C.

Workup

  1. temperatureunder heating at a temperature of from 80° to 90° C. for from 4 to 5 hours
  2. distillationThe solvent was distilled off
  3. additiona dilute potassium carbonate aqueous solution was added to the residue
  4. washThe mixture was washed with chloroform
  5. extractionextracted with chloroform
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off
  8. customto obtain a crude product of the
  9. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-369f67f8fe364a78a2c7d10ddf560a3e
Source dataset
uspto-grants-1994_11
Patent number
USRE034779

Reaction notes

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