2-Aminophenol → N-(2-Hydroxyphenyl)-4-methylbenzene-1-sulfonamide

HRID 896970Notes

Reaction equation

HRID 896970 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(N(CC)CC)C.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CC(C)=O>[OH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 284336N-(2-Hydroxyphenyl)-4-methylbenzene-1-sulfonamideYield 49.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A flask with a stirrer was charged with 10.9 g of 2-aminophenol, 10.1 g of triethylamine and 100 ml of acetone, and a solution of 19.1 g of p-toluenesulfonyl chloride in 50 ml of acetone was dropwise added with cooling with ice over 30 minutes. After completion of the addition, the reaction mixture was stirred at room temperature for 2 hours and then poured into 500 ml of ice water. A precipitated crystal was recovered by filtration and washed with water. The obtained crystal was recrystallized from ethyl acetate/n-hexane mixed solvents, to give 13.0 g of an end product. Melting point 140.0° C.

Workup

  1. temperaturewith cooling with ice over 30 minutes
  2. additionAfter completion of the addition
  3. filtrationA precipitated crystal was recovered by filtration
  4. washwashed with water
  5. customThe obtained crystal was recrystallized from ethyl acetate/n-hexane mixed solvents

Sources & evidence

ORD record
ord-f189a3d819e44b719a13a3da3db9d504
Source dataset
uspto-grants-2005_07
Patent number
US06921740B1

Reaction notes

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