Phenol → 2-Hydroxybenzene-1-sulfonamide

HRID 1034304Notes

Reaction equation

HRID 1034304 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].[C:8]1([OH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C[N+]([O-])=O>[OH:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:2]([NH2:5])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 996PhenolHCID 70918Chlorosulfonyl isocyanateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 6375462-Hydroxybenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of chlorosulfonylisocyanate (Aldrich; 2 mL) in 76 mL MeNO2 at 0° C. was added phenol (2 g) in 10 mL MeNO2. The solution was heated at 45° C. for 30 minutes then AlCl3 (3.46 g) was added and the temperature raised to 100° C. for 30 minutes. The reaction mixture was poured onto ice/H2O, extracted (2× Et2O), and washed with H2O. The organic layer was extracted with K2CO3 (saturated solution) and the aqueous phase then acidified with 1N HCl. Extraction of the aqueous phase with Et2O followed by drying (MgSO4) and evaporation yielded a black oil. Purification of this oil by chromatography (hexane/EtOAc 1:1) gave the title compound as a white solid.

Workup

  1. temperaturethe temperature raised to 100° C. for 30 minutes
  2. additionThe reaction mixture was poured onto ice/H2O
  3. extractionextracted (2× Et2O)
  4. washwashed with H2O
  5. extractionThe organic layer was extracted with K2CO3 (saturated solution)
  6. extractionExtraction of the aqueous phase with Et2O
  7. customby drying
  8. custom(MgSO4) and evaporation
  9. customyielded a black oil
  10. customPurification of this oil by chromatography (hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-548d62177f1248aeba90b387973e1f23
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

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