p-Toluenesulfonic acid → HCID 69616474, compound

HRID 2212249Notes

Reaction equation

HRID 2212249 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8](OC)(OC)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C>[CH3:6][O:7][C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[N:5][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 69720Trimethyl orthobeznoateHCID 72879Methanesulfonamide

Product 1

HCID 69616474HCID 69616474, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methanesulfonamide (4.75 g, 50 mmol)) and trimethyl orthobenzoate (18.2 g, 100 mmol) was heated at 120° C. for 4 h in the presence of a catalytic amount of p-toluenesulfonic acid (50 mg). After being cooled to room temperature, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with a saturated sodium bicarbonate aqueous solution and then water. The organic phase was dried over MgSO4, concentrated, and the resulting residue was treated with hexanes (100 mL) with stirring overnight. A white solid formed was filtered and washed with hexanes to yield a pure N-(methoxyphenylmethylene)methansulfonamide.

Workup

  1. washwashed with a saturated sodium bicarbonate aqueous solution
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. additionthe resulting residue was treated with hexanes (100 mL)
  5. customA white solid formed
  6. filtrationwas filtered
  7. washwashed with hexanes

Sources & evidence

ORD record
ord-53b0b1151da74304a93dae63cc1fab4e
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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