Acetone Cyanohydrin → HCID 178428874, compound

HRID 1386892Notes

Reaction equation

HRID 1386892 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1[C:25]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[C:24]([S:36]([CH3:39])(=[O:38])=[O:37])[CH:23]=[CH:22][C:18]=1[C:19](O)=[O:20].[CH3:40][C:41]([N:44]1[C:48]([OH:49])=[CH:47][CH:46]=[N:45]1)([CH3:43])[CH3:42].C(N(CC)CC)C.CC(C)(O)C#N>C(#N)C>[CH3:40][C:41]([N:44]1[C:48]([OH:49])=[C:47]([C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:24]([S:36]([CH3:39])(=[O:37])=[O:38])=[C:25]([C:26]3[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:28][CH:27]=3)[C:17]=2[CH3:16])[CH:46]=[N:45]1)([CH3:43])[CH3:42]

Participants

7

Reactant 5

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 211831432-Methyl-4-methylsulfonyl-3-(4-methylsulfonylphenyl)benzoic acidHCID 178448738HCID 178448738, compound

Product 1

HCID 178428874HCID 178428874, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

A solution of 560 mg (2.7 mmol) of 1,3-dicyclohexylcarbodiimide in 5 mL of acetonitrile was added with stirring to a mixture of 2-methyl-4-methylsulfonyl-3-(4-methylsulfonylphenyl)benzoic acid and 378 mg (2.7 mmol) of 1-(1,1-dimethylethyl)-5-hydroxypyrazole in 15 mL of acetonitrile. The mixture was allowed to react for 1 hour and was then filtered. The solids were washed with a little acetonitrile. Triethylamine (1.13 mL, 8.1 mmol) and 274 microliters (2.7 mmol) of acetone cyanohydrin were added with stirring to the combined filtrate and acetonitrile wash. After 3 hours, the mixture was diluted with dichloromethane and the resulting solution was washed with 2N aqueous hydrochloric acid, filtered, and concentrated by evaporation under reduced pressure. The residue was dissolved in the minimum amount of hot ethanol and the solution was then cooled. The precipitate that formed was collected by filtration and dried to obtain the title compound as a pale yellow powder melting at 187-188° C.

Workup

  1. customto react for 1 hour
  2. filtrationwas then filtered
  3. washThe solids were washed with a little acetonitrile
  4. washwash
  5. additionthe mixture was diluted with dichloromethane
  6. washthe resulting solution was washed with 2N aqueous hydrochloric acid
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation under reduced pressure
  9. dissolutionThe residue was dissolved in the minimum amount of hot ethanol
  10. temperaturethe solution was then cooled
  11. customThe precipitate that formed
  12. filtrationwas collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-3917d433aea04a878d09156fa5ce3f2c
Source dataset
uspto-grants-2001_07
Patent number
US06265606B1

Reaction notes

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