Ethanol → HCID 67281000, compound

HRID 1693083Notes

Reaction equation

HRID 1693083 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S([O-])(=O)=O)=[CH:3][CH:2]=1.[NH+:12]1[CH:17]=CC=[CH:14][CH:13]=1.[CH2:18]([OH:20])[CH3:19].[OH2:21]>>[OH:21][C:4]1[CH:5]=[CH:6][C:1]([C:11]2[CH:14]=[CH:13][N:12]([CH3:17])[C:18](=[O:20])[CH:19]=2)=[CH:2][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 67281000HCID 67281000, compoundYield 70%

Procedure

Pyridinium p-toluenesulfonate (2.67 g, 10.6 mmol) was added to an ethanol (15 mL) solution of the compound (1.01 g, 3.54 mmol) obtained in the above reaction, and stirred at room temperature for 19 hours. Water was added to the reaction mixture, the precipitated substance was taken out through filtration, washed with diethyl ether, and dried to obtain the entitled compound (500 mg, 70%) as a colorless solid. Further, the filtrate was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the entitled compound (195 mg, 27%).

Workup

  1. customobtained in the above reaction
  2. filtrationthe precipitated substance was taken out through filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-e25b02870845404caaa92bc1c5cc0e8a
Source dataset
uspto-grants-2012_04
Patent number
US08158652B2

Reaction notes

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