Ethyl Acetate → 4-(2-Hydroxyethanesulfonyl)benzene-1-sulfonamide

HRID 2118577Notes

Reaction equation

HRID 2118577 reaction equation
OCCS[C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.OO[S:17]([O-:19])=[O:18].[K+].[C:21](OCC)(=[O:23])[CH3:22]>O>[OH:23][CH2:21][CH2:22][S:17]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:12])=[O:13])=[CH:7][CH:6]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 42697544-[(2-Hydroxyethyl)sulfanyl]benzenesulfonamideHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 139603484-(2-Hydroxyethanesulfonyl)benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(2-Hydroxyethylthio)benzenesulfonamide (94.3 g, 0.40 mol) was added portionwise to a stirred solution of Oxone® (368.9 g, 0.60 mols) in H2O (3600 mL). After 18 hours the white solid was collected, washed with H2O and dried to give 72.6 g, mp 156°-162° C. An additional 12.3 g was obtained from the aqueous filtrate by extraction with ethyl acetate (3×1000 mL). Recrystallization from acetonitrile gave material with mp 163°-165° C.

Workup

  1. customAfter 18 hours the white solid was collected
  2. washwashed with H2O
  3. customdried
  4. customto give 72.6 g, mp 156°-162° C
  5. customRecrystallization from acetonitrile
  6. customgave material with mp 163°-165° C.

Sources & evidence

ORD record
ord-2ff7eca796c047eb99a6e5e05b79b1e9
Source dataset
uspto-grants-1987_07
Patent number
US04678855

Reaction notes

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