2-Aminophenol → HCID 22346066, compound

HRID 896975Notes

Reaction equation

HRID 896975 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([N:11]([CH2:14][CH3:15])CC)C.[C:16]1([C:26]2[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>O1CCCC1>[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]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([NH:11][C:14]3[CH:15]=[CH:6][CH:7]=[CH:2][C:3]=3[OH:8])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 8471TriethylamineHCID 76950(1,1'-Biphenyl)-4,4'-disulfonyl dichloride

Product 1

HCID 22346066HCID 22346066, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flask with a stirrer was charged with 3.10 g of 2-aminophenol, 2.87 g of triethylamine and 50 ml of tetrahydrofuran, and a solution of 5.00 g of 4,4′-biphenyldisulfonyl chloride in 10 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 3.7 g of an end product. Decomposition point 185° 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-308fbc16ed7343458b63177ff67798aa
Source dataset
uspto-grants-2005_07
Patent number
US06921740B1

Reaction notes

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