2-Aminophenol → HCID 789223, compound

HRID 896973Notes

Reaction equation

HRID 896973 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.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>O1CCCC1>[OH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:23]([C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 789223HCID 789223, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flask with a stirrer was charged with 5.46 g of 2-aminophenol, 5.05 g of triethylamine and 100 ml of tetrahydrofuran, and a solution of 10.55 g of 4-chlorobenzenesulfonyl chloride in 20 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 8.9 g of an end product. Melting point 82° 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-cd5152d1048f4f03a3d714fe22c14525
Source dataset
uspto-grants-2005_07
Patent number
US06921740B1

Reaction notes

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