2-Aminophenol → HCID 3906170, compound

HRID 896974Notes

Reaction equation

HRID 896974 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.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>O1CCCC1>[OH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:23][CH:22]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 3906170HCID 3906170, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flask with a stirrer was charged with 8.18 g of 2-aminophenol, 7.58 g of triethylamine and 100 ml of tetrahydrofuran, and a solution of 15.50 g of 4-methoxybenzenesulfonyl chloride in 30 ml of tetrahydrofuran was dropwise added with cooling with ice over 10 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 ethanol/n-hexane mixed solvents, to give 9.8 g of an end product. Melting point 89° C.

Workup

  1. temperaturewith cooling with ice over 10 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 ethanol/n-hexane mixed solvents

Sources & evidence

ORD record
ord-c1c83f6ace99400f8d9b73215b2dd211
Source dataset
uspto-grants-2005_07
Patent number
US06921740B1

Reaction notes

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