Methanesulfonyl chloride → N-(3-cyanomethyl-2-methyl-phenyl)-methanesulfonamide

HRID 1106741Notes

Reaction equation

HRID 1106741 reaction equation
[NH2:1][C:2]1[C:3]([CH3:11])=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>N1C=CC=CC=1>[C:9]([CH2:8][C:4]1[C:3]([CH3:11])=[C:2]([NH:1][S:13]([CH3:12])(=[O:15])=[O:14])[CH:7]=[CH:6][CH:5]=1)#[N:10]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 221703203-Amino-2-methylphenylacetonitrile

Product 1

HCID 18789726N-(3-cyanomethyl-2-methyl-phenyl)-methanesulfonamideYield 94.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3-Amino-2-methyl-phenyl)-acetonitrile (11.1 g) was dissolved in 80 ml of pyridine. The solution was cooled in an ice bath and 11.3 g of methanesulfonyl chloride was added. The reaction mixture was removed from the ice bath and stirred at room temperature for 30 minutes; 10 ml of water was added, and the mixture was stirred for 30 minutes, poured into ethyl acetate (EtOAc), washed with cold hydrochloric acid, washed with water, dried, and evaporated to give 16.1 g of N-(3-cyanomethyl-2-methyl-phenyl)-methanesulfonamide as a light yellow solid. ##STR120##

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe reaction mixture was removed from the ice bath
  3. addition10 ml of water was added
  4. stirringthe mixture was stirred for 30 minutes
  5. additionpoured into ethyl acetate (EtOAc)
  6. washwashed with cold hydrochloric acid
  7. washwashed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-ab1d31a3f8484ee4815a227d25ae1cb0
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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