Hydrochloric Acid → HCID 178463117, compound

HRID 399939Notes

Reaction equation

HRID 399939 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:16]([N:18]1[C:22]([OH:23])=[CH:21][CH:20]=[N:19]1)[CH3:17].C1(N=C=NC2CCCCC2)CCCCC1.Cl>C(#N)C>[CH2:16]([N:18]1[C:22]([OH:23])=[C:21]([C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:10]([Cl:11])[C:2]=2[Cl:1])[CH:20]=[N:19]1)[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 27869432,3-dichloro-4-methylsulfonylbenzoic acidHCID 178418331HCID 178418331, compound

Product 1

HCID 178463117HCID 178463117, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 500 mg (1.85 mmol) of 2,3-dichloro-4-methylsulfonylbenzoic acid and 240 mg (2.14 mmol) of 1-ethyl-5-hydroxypyrazole in 10 mL of dry acetonitrile was treated with 430 mg (2.08 mmol) of dicyclohexylcarbodiimide with stirring at ambient temperature for 0.5 hr. The precipitate that formed was removed by filtration and the filtrate was treated with 0.5 mL of triethylamine and 1 mL of acetone cyanohydrin. After 1 hr, the reaction mixture was partitioned between dichloromethane and 1N aqueous hydrochloric acid. The organic layer was extracted with dilute aqueous sodium bicarbonate solution and the basic aqueous solution obtained was acidified with dilute aqueous hydrochloric acid and extracted with dichloromethane. The organic extract was dried over sodium sulfate and concentrated by evaporation under reduced pressure to obtain 540 mg (81 percent of theory) of the title compound as an orange syrup.

Workup

  1. customThe precipitate that formed
  2. customwas removed by filtration
  3. additionthe filtrate was treated with 0.5 mL of triethylamine and 1 mL of acetone cyanohydrin
  4. waitAfter 1 hr
  5. customthe reaction mixture was partitioned between dichloromethane and 1N aqueous hydrochloric acid
  6. extractionThe organic layer was extracted with dilute aqueous sodium bicarbonate solution
  7. customthe basic aqueous solution obtained
  8. extractionextracted with dichloromethane
  9. extractionThe organic extract
  10. dry with materialwas dried over sodium sulfate
  11. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-e2c2b14ddd1e425e867e66d25953fde8
Source dataset
uspto-grants-1998_10
Patent number
US05824802

Reaction notes

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