Hydrochloric Acid → 2-(Acetoxymethyl)benzenesulfonamide

HRID 1155635Notes

Reaction equation

HRID 1155635 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10].[C:13]([O-:16])(=[O:15])[CH3:14].[K+].Cl>O>[C:13]([O:16][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517044Potassium AcetateHCID 133646272-(Chloromethyl)benzenesulfonamide

Product 1

HCID 130973012-(Acetoxymethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(chloromethyl)benzenesulfonamide (2.00 g), potassium acetate (6.0 g) and water (75 ml) was heated to reflux for 1.5 hour. The pH was adjusted to ca. 5.0 by addition of hydrochloric acid and the chilled mixture was filtered to give 1.05 of of shiny white solid, m.p. 131°-133°. 'H NMR δ(CD3)2CO 8.00-7.83 (M), 7.60-7.25 (M), 6.55 (brd s), 5.47 (s), 2.97 (brd s), 2.10 (s), consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hour
  3. filtrationthe chilled mixture was filtered
  4. customto give 1.05 of of shiny white solid, m.p. 131°-133°

Sources & evidence

ORD record
ord-439f86cf23e941daa85e51b148807256
Source dataset
uspto-grants-1982_06
Patent number
US04332611

Reaction notes

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