4-Aminophenol → HCID 19039291, compound

HRID 1608545Notes

Reaction equation

HRID 1608545 reaction equation
[CH2:1]([S:19]([O-:22])(=[O:21])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Na+].S(Cl)(Cl)=O.[CH:28]1[C:33]([NH2:34])=[CH:32][CH:31]=[C:30]([OH:35])[CH:29]=1.C(N(CC)CC)C>CN(C)C=O.O>[CH2:1]([S:19]([NH:34][C:33]1[CH:28]=[CH:29][C:30]([OH:35])=[CH:31][CH:32]=1)(=[O:21])=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 4034-AminophenolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 236680031-Octadecanesulfonic acid, sodium salt (1:1)

Product 1

HCID 19039291HCID 19039291, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen atmosphere, sodium octadecanesulfonate (357 g) was suspended in dimethylformamide (600 ml) and thereto was added dropwise thionyl chloride (119 g) over a period of about 30 minutes. After completion of the addition, the suspension was heated at 80° C. for 1 hour to prepare the corresponding sulfonic acid chloride. The reaction mixture was cooled and thereto were added p-aminophenol (109 g) and triethylamine (202 g), followed by refluxing with heating for 3 hours. After completion of the reaction, the reaction mixture was poured into water to precipitate a white solid. Thereto was added 5% hydrochloric acid to adjust the pH to acidic state and then, the white solid was filtered off under reduced pressure and then recrystallized from methyl ethyl ketone to obtain the desired product (302 g). Yield 71%; m.p. 142° C.

Workup

  1. additionAfter completion of the addition
  2. temperatureThe reaction mixture was cooled
  3. temperatureby refluxing
  4. temperaturewith heating for 3 hours
  5. customAfter completion of the reaction
  6. customto precipitate a white solid
  7. additionThereto was added 5% hydrochloric acid
  8. filtrationthe white solid was filtered off under reduced pressure
  9. customrecrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-19d804c8140b4e77aef2d787db5dce69
Source dataset
uspto-grants-1995_03
Patent number
US05395815

Reaction notes

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