Hydrochloric Acid → HCID 23508380, compound

HRID 1883671Notes

Reaction equation

HRID 1883671 reaction equation
CS([O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][CH:7]=1)(=O)=O.C[O-].[Na+].O1CCCC1.Cl>CO>[OH:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:12]([C:9]2[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=2)[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 23508424HCID 23508424, compound

Product 1

HCID 23508380HCID 23508380, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture composed of 80 mg of 4-[N-(4-hydroxybenzyl)-N-methylsulfonylamino]phenyl methanesulfonate and 0.5 ml of a 28% methanolic solution of sodium methoxide was stirred in 2 ml of methanol and 1 ml of tetrahydrofuran at 50° C. for 1hour. After hydrochloric acid was added to the reaction mixture, the product was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. After the solvent was distilled off the resulting crude product was purified by TLC (using a 19:1 mixture of chloroform and methanol as the developing solvent) to obtain 38 mg of N-(4-hydroxybenzyl)-N-(4-hydroxyphenyl)methanesulfonamide.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off the resulting crude product
  5. customwas purified by TLC (
  6. additiona 19:1 mixture of chloroform and methanol as the developing solvent)

Sources & evidence

ORD record
ord-55c0d43bf4bb4e05802f0e0efd39347d
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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