Water → HCID 53888739, compound

HRID 327690

Reaction equation

HRID 327690 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13].N1C=CC=CC=1.[CH3:21][NH:22][S:23](Cl)(=[O:25])=[O:24].O>C(Cl)Cl>[OH:14][CH:11]([CH2:10][O:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:2][CH3:1])[CH2:12][O:13][S:23](=[O:25])(=[O:24])[NH:22][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 3516GuaifenesinHCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 53888739HCID 53888739, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 26.5 g (0.13 mole) of glycerol guaiacolate in 100 ml of methylene chloride and 10.8 ml (0.13 mole) of pyridine was added in a thin stream to a stirred solution of 17.1 g (0.13 mole) of N-methylsulfamoyl chloride (Preparation 24) in 70 ml of methylene chloride, and the reaction mixture was stirred at ambient temperature for 2 hr. The reaction mixture was treated with 150 ml of water, the layers were separated, and the organic layer was washed successively with a 200 ml portion of 2N hydrochloric acid solution, four 200 ml portions of water, dried (magnesium sulfate), and the solvent was evaporated under reduced pressure to yield a viscous oil. The oil was purified by preparative high pressure liquid chromatography. Fractions containing the desired product were combined and the solvents evaporated under reduced pressure to give 13.9 g (37%) of the title compound as a yellow gum.

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed successively with a 200 ml portion of 2N hydrochloric acid solution, four 200 ml portions of water
  3. dry with materialdried (magnesium sulfate)
  4. customthe solvent was evaporated under reduced pressure
  5. customto yield a viscous oil
  6. customThe oil was purified by preparative high pressure liquid chromatography
  7. additionFractions containing the desired product
  8. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-97ec3988ea2d4813aff2b3593cae75cd
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Linked notes

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