Dicyclohexylcarbodiimide → HCID 178463132, compound

HRID 369581Notes

Reaction equation

HRID 369581 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[C:25]([O:26][CH:27]2[CH2:30][O:29][CH2:28]2)=[C:24]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=O.[CH2:35]([N:37]1[C:41]([OH:42])=[CH:40][CH:39]=[N:38]1)[CH3:36].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CC(C)(O)C#N.O>[CH2:35]([N:37]1[C:41]([OH:42])=[C:40]([C:19](=[O:21])[C:18]2[CH:22]=[CH:23][C:24]([S:31]([CH3:34])(=[O:33])=[O:32])=[C:25]([O:26][CH:27]3[CH2:30][O:29][CH2:28]3)[C:17]=2[Cl:16])[CH:39]=[N:38]1)[CH3:36]

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 232823422-Chloro-4-methylsulfonyl-3-(3-oxetanyloxy)benzoic acidHCID 178418331HCID 178418331, compound

Product 1

HCID 178463132HCID 178463132, compound

Reagents, catalysts & solvents 3

HCID 6406Acetone CyanohydrinCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Dicyclohexylcarbodiimide (0.72 g (3.5 mmol) was added at ambient temperature with stirring to a solution of 1.07 g (3.5 mmol) of 2-chloro-4-methylsulfonyl-3-(3-oxetanyloxy)benzoic acid and 0.45 g (4 mmol) of 1-ethyl-5-hydroxypyrazole in 25 mL of dry acetonitrile. The mixture was allowed to react for about one hour and then was filtered. The solids collected were extracted with dry acetonitrile. The filtrate and extract were combined and 0.69 g (5.0 mmol) of potassium carbonate and a few drops of acetone cyanohydrin were added with stirring at ambient temperature. The mixture was stirred overnight and was then poured into water. The resulting solution was extracted with ether and then acidified with aqueous hydrochloric acid. The mixture obtained was extracted three times with dichloromethane and the three extracts were combined, washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The yellow solid residue was recrystallized from ethanol to obtain 0.77 g (55 percent of theory) of the title compound as a nearly colorless solid melting at 206-2080° C.

Workup

  1. customto react for about one hour
  2. filtrationwas filtered
  3. customThe solids collected
  4. extractionwere extracted with dry acetonitrile
  5. extractionThe filtrate and extract
  6. stirringThe mixture was stirred overnight
  7. extractionThe resulting solution was extracted with ether
  8. customThe mixture obtained
  9. extractionwas extracted three times with dichloromethane
  10. washwashed with water
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated by evaporation under reduced pressure
  13. customThe yellow solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-498d8e3dc611407d9a3a068c47567876
Source dataset
uspto-grants-2000_10
Patent number
US06140271

Reaction notes

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