3-Aminophenol → N-(3-hydroxyphenyl)methanesulfonamide

HRID 1048721Notes

Reaction equation

HRID 1048721 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][S:10](Cl)(=[O:12])=[O:11]>N1C=CC=CC=1>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][S:10]([CH3:9])(=[O:12])=[O:11])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 31297Methanesulfonyl chloride

Product 1

HCID 836758N-(3-hydroxyphenyl)methanesulfonamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

2 g (18.33 mmol) of 3-aminophenol were dissolved in 6 ml of pyridine with magnetic stirring, the mixture was cooled to 10° C. and then 1.8 ml (23.26 mmol) of methanesulfonyl chloride were added. The cold bath was withdrawn and the mixture was stirred at r.t. for 18 h before being diluted with 100 ml of a saturated NaCl aqueous solution. The aqueous phase was extracted with 100 ml of ethyl acetate. The organic phase was washed with 50 ml of a saturated NaHCO3 aqueous solution, extracted with 50 ml of an aqueous solution of NaOH (0.5 N). The basic aqueous phase was washed with 2×100 ml of ethyl acetate and then acidified down to pH 2-3 by adding a 1N HCl aqueous solution. The acidified aqueous phase was extracted with 2×100 ml of ethyl acetate. The combined organic phases were washed with 100 ml of a saturated NaCl aqueous solution and then dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. 3.3 g (yield=80%) of N-(3-hydroxyphenyl)methanesulfonamide were obtained as an oil. LC-MS: m/z=186 (M-H+); UV purity at 254 nm=81%.

Workup

  1. customThe cold bath was withdrawn
  2. additionbefore being diluted with 100 ml of a saturated NaCl aqueous solution
  3. extractionThe aqueous phase was extracted with 100 ml of ethyl acetate
  4. washThe organic phase was washed with 50 ml of a saturated NaHCO3 aqueous solution
  5. extractionextracted with 50 ml of an aqueous solution of NaOH (0.5 N)
  6. washThe basic aqueous phase was washed with 2×100 ml of ethyl acetate
  7. additionby adding a 1N HCl aqueous solution
  8. extractionThe acidified aqueous phase was extracted with 2×100 ml of ethyl acetate
  9. washThe combined organic phases were washed with 100 ml of a saturated NaCl aqueous solution
  10. customdried on Na2SO4 which
  11. customwas then removed by filtration
  12. concentrationThe obtained filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4197e8da3f8d4220820b025fd6a3fcd7
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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