Ethyl Acetate → N-(3-cyanomethoxyphenyl)methanesulfonamide

HRID 618204Notes

Reaction equation

HRID 618204 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. ##STR56##

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-f15fe224e1924b44a333b35f6076a76c
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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