Water → HCID 11265881, compound

HRID 337345Notes

Reaction equation

HRID 337345 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>ClCCl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:9][C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[NH2:1])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 760822-Amino-5-methylphenol

Product 1

HCID 11265881HCID 11265881, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 mg of 2-amino-5-methylphenol was dissolved in 6.5 ml of dichloromethane, and 476 μl of triethylamine and 619 mg of p-toluene sulfonylchloride were added and stirred at room temperature for 1 hour. To the reaction mixture, 60 ml of water was added, and extracted with 60 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified using silica gel column chromatography (hexane:ethyl acetate=3:1) to yield 730.1 mg of the title compound.

Workup

  1. extractionextracted with 60 ml of ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. custompurified

Sources & evidence

ORD record
ord-3aa7100c9bdd4d7a9e9a4f41bf40288f
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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