Hydrochloric Acid → HCID 14819602, compound

HRID 476743Notes

Reaction equation

HRID 476743 reaction equation
[CH:1]1([S:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[NH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:15]([S:17](Cl)(=[O:19])=[O:18])[CH3:16].Cl>N1C=CC=CC=1>[CH:1]1([S:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[NH:10][S:17]([CH2:15][CH3:16])(=[O:19])=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11667Ethanesulfonyl chlorideHCID 14771321HCID 14771321, compound

Product 1

HCID 14819602HCID 14819602, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 10 ml of pyridine was dissolved 2.0 g of 2-(cyclohexylthio)aniline obtained in Example 2 (2), 1.2 g of ethanesulfonyl chloride was added dropwise under ice cooling, and then the mixture was stirred at room temperature overnight. The reaction solution was poured into ice water, made acidic with dilute hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed, in turn, with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent:n-hexaneethyl acetate=10:1) to give 2.7 g of N-[2-(cyclohexylthio)phenyl]ethanesulfonamide as an oil.

Workup

  1. additionwas added dropwise under ice cooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed, in turn, with water
  4. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel column chromatography (eluent:n-hexaneethyl acetate=10:1)

Sources & evidence

ORD record
ord-58092992c7d64df584353f7a360db90d
Source dataset
uspto-grants-1989_12
Patent number
US04885367

Reaction notes

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