Sodium Carbonate → Dimethylsulfamic acid 2-[4-(1H-imidazol-1-yl)phenoxy]ethyl ester

HRID 327737Notes

Reaction equation

HRID 327737 reaction equation
[N:1]1([C:6]2[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][OH:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH3:18][N:19]([CH3:24])[S:20](Cl)(=[O:22])=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[N:1]1([C:6]2[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][O:13][S:20](=[O:22])(=[O:21])[N:19]([CH3:24])[CH3:18])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 100816222-[4-(1H-imidazol-1-yl)phenoxy]ethanol

Product 1

HCID 54128900Dimethylsulfamic acid 2-[4-(1H-imidazol-1-yl)phenoxy]ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 15.0 g (0.074 mol) of 2-[4-(1H-imidazol-1-yl)phenoxy]ethanol in 100 mL of N,N-dimethylformamide (DMF) was added 3.8 g (0.1 mol) of sodium hydride (60% oil dispersion) portionwise and the mixture was stirred at ambient temperature for 3 h. To this mixture was added 13.7 g (0.1 mol) of dimethylsulfamoyl chloride and the mixture was stirred at ambient temperature overnight. The reaction mixture was poured into 1.2 L of water and its pH was adjusted to 10 with sodium carbonate. The mixture was extracted with three 400-mL portions of ethyl acetate. The combined organic layers were washed twice with 400-mL portions of water, dried (MgSO4), and the solvent was evaporated under reduced pressure to give a viscous residue. The residue was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500 A; PrepPAK 500 silica; ethyl acetate; flow rate 150 mL/min). Fractions containing the product were combined and the solvent was evaporated under reduced pressure to give the title compound, a viscous oil. The oil was converted to the hydrochloride (2-propanol; ethereal HCl) and the white solid was collected by filtration to yield 5.9 g (26%), mp 120°-123° C.

Workup

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. extractionThe mixture was extracted with three 400-mL portions of ethyl acetate
  3. washThe combined organic layers were washed twice with 400-mL portions of water
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customto give a viscous residue
  7. customThe residue was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500 A; PrepPAK 500 silica; ethyl acetate; flow rate 150 mL/min)
  8. additionFractions containing the product
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1719d607af2a49feafde3ec6babcae35
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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