Water → HCID 22316930, compound

HRID 910220Notes

Reaction equation

HRID 910220 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C1(C)C=CC(S([CH2:21][N:22]=C=O)(=O)=O)=CC=1.[C:26](=O)([O-])[O-].[K+].[K+].O>CO>[O:3]1[C:1]([C:4]2[CH:11]=[CH:10][C:7]([C:8](=[O:9])[CH3:26])=[CH:6][CH:5]=2)=[CH:2][N:22]=[CH:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5009465Benzaldehyde, 4-acetyl-HCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzene

Product 1

HCID 22316930HCID 22316930, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Acetylbenzaldehyde (2.96 g) and p-toluenesulfonylmethylisocyanate (4.69 g) were dissolved in methanol (200 mL). Potassium carbonate (3.32 g) was added to the solution, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The solvent was evaporated, and the residue was purified through silica gel column chromatography (dichloromethane:methanol=100:1), followed by concentration under reduced pressure, to thereby yield the title compound (3.14 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. customThe solvent was evaporated
  3. customthe residue was purified through silica gel column chromatography (dichloromethane:methanol=100:1)
  4. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-237d81c8fa0d45dd944acb723a4abb9f
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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