Hydrochloric Acid → Sulfamic acid 2-[3(1H-imidazol-1-yl)phenoxy]ethyl ester

HRID 1613434Notes

Reaction equation

HRID 1613434 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].[N:6]1([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[O:14][CH2:15][CH2:16][OH:17])[CH:10]=[CH:9][N:8]=[CH:7]1.Cl>C(#N)C>[N:6]1([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[O:14][CH2:15][CH2:16][O:17][S:1](=[O:4])(=[O:3])[NH2:2])[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24499Chlorosulfamic acidHCID 100587282-[3-(1H-Imidazol-1-yl)phenoxy]ethanol

Product 1

HCID 10062358Sulfamic acid 2-[3(1H-imidazol-1-yl)phenoxy]ethyl esterYield 56.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of sulfamoyl chloride (0.0275 mole) in 60 ml of acetonitrile was treated dropwise with a solution of 5.1 g (0.025 mole) of 2-[3(1H-imidazol-1-yl)phenoxy]ethanol in 100 ml of acetonitrile. The mixture was stirred at ambient temperature under nitrogen for 20 hr. The mixture was concentrated under vacuum, and the residue was partitioned between ethyl acetate and dilute potassium carbonate solution. The organic fraction was again concentrated under vacuum to a crystalline residue. This residue was dissolved in warm 95% ethanol and treated with 1 equivalent of anhydrous hydrogen chloride. The solution was chilled and the precipitate was collected and dried to give 4.0 g (50%) of the title compound as a pinkish powder, monohydrochloride, mp 149.0°-150.0° C.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate and dilute potassium carbonate solution
  3. concentrationThe organic fraction was again concentrated under vacuum to a crystalline residue
  4. dissolutionThis residue was dissolved in warm 95% ethanol
  5. temperatureThe solution was chilled
  6. customthe precipitate was collected
  7. customdried

Sources & evidence

ORD record
ord-5d52bfa353624369abdd191bd439583b
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

Loading…