Triethylamine → 2-(Methylsulfonamido)phenylacetonitrile

HRID 656270Notes

Reaction equation

HRID 656270 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl.Cl>[CH3:18][S:19]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10])(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 76307Phenylglycine nitrile

Product 1

HCID 691184052-(Methylsulfonamido)phenylacetonitrileYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 2-aminophenylacetonitrile (500 mg) in dichloromethane (20 ml) were added triethylamine (330 μl) and methanesulfonyl chloride (530 μl) and the mixture was stirred for 16 hours, under argon gas atmosphere. After confirming the completion of the reaction using TLC, the resulting mixture was diluted with 1 N aqueous hydrochloric acid solution (30 ml), and extracted with dichloromethane (50 ml×3). The organic layer was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by column-chromatography (ethyl acetate/hexane=1/2) to yield (2-methanesulfonylaminophenyl)acetonitrile (573 mg, 72%).

Workup

  1. extractionextracted with dichloromethane (50 ml×3)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by column-chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-4588ec9644734059be1e44ba1f13a93e
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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