p-Toluenesulfonic acid → 5-Cyanomethyl-2-methoxybenzenesulfonamide

HRID 2232024Notes

Reaction equation

HRID 2232024 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:18][CH3:19])=[C:8]([S:10]([NH:13]C(C)(C)C)(=[O:12])=[O:11])[CH:9]=1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:18][CH3:19])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1)#[N:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 139214545-Cyanomethyl-N-(1,1-dimethylethyl)-2-methoxybenzenesulfonamide

Product 1

HCID 139214555-Cyanomethyl-2-methoxybenzenesulfonamideYield 20.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3.0 g of the compound from Example 2 and 0.1 g p-toluenesulfonic acid in 100 ml of dry toluene was refluxed in a flask equipped with a Dean-Stark apparatus. After being refluxed overnight the solution was concentrated and allowed to cool. The precipitate was filtered off to give 0.5 g light brown solid. The mother liquor was chromatographed over silica gel with 20:73:2:5, ethyl acetate:methylene chloride:methanol:THF to give additional product, m.p. 173°-177° C.;

Workup

  1. temperaturewas refluxed in a flask
  2. customequipped with a Dean-Stark apparatus
  3. temperatureAfter being refluxed overnight the solution
  4. concentrationwas concentrated
  5. temperatureto cool
  6. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-c3fcae96019748a7b0d7e2e0850fb344
Source dataset
uspto-grants-1988_11
Patent number
US04786314

Reaction notes

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