Hydrochloric Acid → N-[2-(Cyclohexyloxy)phenyl]methanesulfonamide

HRID 476735

Reaction equation

HRID 476735 reaction equation
[CH:1]1([O: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.[CH3:15][S:16](Cl)(=[O:18])=[O:17].Cl>N1C=CC=CC=1>[CH:1]1([O:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[NH:10][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 14771305HCID 14771305, compound

Product 1

HCID 14771306N-[2-(Cyclohexyloxy)phenyl]methanesulfonamideYield 89.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 20 ml of a pyridine solution containing 2.7 g of 2-cyclohexyloxyaniline was added dropwise 1.8 g of methanesulfonyl chloride under ice cooling with stirring. After completion of the addition, the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into ice water and made acidic with dilute hydrochloric acid. The crystals which formed were collected by filtration, washed with water and dried to give 3.8 g of the crude crystals, which were then recrystallized from ethanol-n hexane to give 3.4 g of N-(2-cyclohexyloxyphenyl)methanesulfonamide.

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customThe crystals which formed
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried
  7. customto give 3.8 g of the crude crystals, which
  8. customwere then recrystallized from ethanol-n hexane

Sources & evidence

ORD record
ord-d60f411f1bd84b318eff2566602610b7
Source dataset
uspto-grants-1989_12
Patent number
US04885367

Linked notes

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