Hydrochloric Acid → HCID 22419887, compound

HRID 1720028Notes

Reaction equation

HRID 1720028 reaction equation
N[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][CH2:10][S:11](Cl)(=[O:13])=[O:12].[N:15]1C=CC=CC=1.Cl>O1CCCC1>[Cl:9][CH2:10][S:11]([NH:15][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[OH:2])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 77054(Chloromethyl)sulfonyl chlorideHCID 2794249O-Phenylhydroxylamine

Product 1

HCID 22419887HCID 22419887, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

O-Aminophenol (43.6 g, 0.40 mol) was dissolved in tetrahydrofuran (200 ml). Chloromethanesulfonyl chloride (61.8 g, 0,415 mol) was slowly added to the solution at room temperature, and the resultant solution, was stirred for 30 minutes. Pyridine (45 ml) was added to the solution, and stirring was continued overnight. The reaction mixture was acidified to pH=1 with hydrochloric acid and extracted with ethyl acetate. The organic extracts were washed with sodium bicarbonate aq. and brine followed by drying over sodium sulfate. The solvent was removed by evaporation, and the residual oil was sitting at room temperature for 2 days to form crystals, which were collected by filtration to afford the titled product, 18.5 g.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with sodium bicarbonate aq. and brine
  3. dry with materialby drying over sodium sulfate
  4. customThe solvent was removed by evaporation
  5. waitthe residual oil was sitting at room temperature for 2 days
  6. customto form crystals, which
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-70dce995a0c844bca6d342688683881c
Source dataset
uspto-grants-1996_04
Patent number
US05504095

Reaction notes

Loading…