2-Aminophenol → HCID 2835149, compound

HRID 896972Notes

Reaction equation

HRID 896972 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.[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[S:26](Cl)(=[O:28])=[O:27]>CC(C)=O>[OH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:26]([C:17]1[CH:18]=[CH:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 71252-Naphthalenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 2835149HCID 2835149, compoundYield 50.2%

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 22.7 g of 2-naphthalenesulfonyl 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 15.0 g of an end product. Melting point 136.0° 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-a893573cbd214970a09809fb9daed0f1
Source dataset
uspto-grants-2005_07
Patent number
US06921740B1

Reaction notes

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