Ethyl Acetate → N-(3-cyanomethoxyphenyl)methanesulfonamide

HRID 1106710Notes

Reaction equation

HRID 1106710 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[O:5][CH2:6][C:7]#[N:8].[CH3:12][S:13](Cl)(=[O:15])=[O:14].C(OCC)(=O)C>N1C=CC=CC=1>[C:7]([CH2:6][O:5][C:4]1[CH:3]=[C:2]([NH:1][S:13]([CH3:12])(=[O:15])=[O:14])[CH:11]=[CH:10][CH:9]=1)#[N:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 187896992-(3-Aminophenoxy)acetonitrile

Product 1

HCID 18789601N-(3-cyanomethoxyphenyl)methanesulfonamideYield 65.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3-Aminophenoxy)-acetonitrile (3.0 g) was dissolved in 12 ml of pyridine, cooled in an ice bath, treated with 3.47 g of methanesulfonyl chloride, and stirred at room temperature for 3 hours. The mixture was poured into ethyl acetate, washed with hydrochloric acid, then with water, dried, and evaporated. The residue was purified by silica gel chromatography eluting with ethyl acetate:hexane (3:7) giving 3.0 g of N-(3-cyanomethoxyphenyl)-methanesulfonamide. An aliquot of this product was crystallized from ethyl acetate:hexane (3:7) to give a solid, mp 91-92° C. ##STR66##

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with hydrochloric acid
  3. dry with materialwith water, dried
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate:hexane (3:7)

Sources & evidence

ORD record
ord-948f35b1af214a02a67b27168652079e
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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