p-Toluenesulfonic acid → HCID 20524766, compound

HRID 1702743Notes

Reaction equation

HRID 1702743 reaction equation
[O:1]=[C:2]([CH3:17])[CH2:3][N:4]([S:13]([CH3:16])(=[O:15])=[O:14])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:29](OC)(OC)[O:30]C.[C:36](=O)(O)[O-].[Na+]>CO>[CH3:36][O:1][C:2]([O:30][CH3:29])([CH3:17])[CH2:3][N:4]([S:13]([CH3:16])(=[O:15])=[O:14])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 20524767HCID 20524767, compound

Product 1

HCID 20524766HCID 20524766, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2-oxopropyl)-2'-chloro-6'-methyl-methanesulphonanilide (5.7 g) in methanol (80 ml) was added 4-toluenesulphonic acid (0.2 g), followed by trimethyl orthoformate (6.65 ml). The mixture was stirred at room temperature for 24 hours, then allowed to stand for 6 days. The solution was poured into dilute sodium bicarbonate solution, and the precipitated solid was collected by filtration, washed with water, and dried to give an off-white coloured solid of melting point 84°. Yield 6.0 g.

Workup

  1. waitto stand for 6 days
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. customto give an off-white coloured solid of melting point 84°

Sources & evidence

ORD record
ord-a3487eee6c59421d99222bd8486edb0e
Source dataset
uspto-grants-1982_09
Patent number
US04349378

Reaction notes

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