Ethyl Acetate → N-(5-cyanomethoxy-2-methylphenyl)-methanesulfonamide

HRID 1106716Notes

Reaction equation

HRID 1106716 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[O:5][CH2:6][C:7]#[N:8].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(OCC)(=O)C>N1C=CC=CC=1>[C:7]([CH2:6][O:5][C:4]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:2]([NH:1][S:14]([CH3:13])(=[O:16])=[O:15])[CH:3]=1)#[N:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 18789626(3-Amino-4-methylphenoxy) acetonitrile

Product 1

HCID 18789597N-(5-cyanomethoxy-2-methylphenyl)-methanesulfonamideYield 90.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

(3-Amino-4-methylphenoxy)-acetonitrile (2.6 g) was dissolved in 10 ml of pyridine, cooled in an ice bath; 2.29 g of methanesulfonyl chloride was added; and the reaction mixture was stirred at 5° C. for 1 hour. The mixture was poured into ethyl acetate, washed with hydrochloric acid, then water, dried, and evaporated giving 3.5 g of N-(5-cyanomethoxy-2-methylphenyl)-methanesulfonamide. ##STR76##

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with hydrochloric acid
  3. dry with materialwater, dried
  4. customevaporated

Sources & evidence

ORD record
ord-ffdedc6a8902449dad56d6d807b284ca
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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