Cesium carbonate → N-(2-cyanophenyl)-N-methylmethanesulfonamide

HRID 1487237Notes

Reaction equation

HRID 1487237 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][NH:8][S:9]([CH3:12])(=[O:11])=[O:10].F[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17]>C(#N)C>[C:16]([C:15]1[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=1[N:8]([CH3:7])[S:9]([CH3:12])(=[O:11])=[O:10])#[N:17]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 678552-FluorobenzonitrileHCID 97632N-Methylmethanesulfonamide

Product 1

HCID 45480189N-(2-cyanophenyl)-N-methylmethanesulfonamideYield 88.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of cesium carbonate (55.78 g, 171 mmol) in acetonitrile (500 mL) at room temperature was added N-methylmethane-sulfonamide (14.0 g, 0.128 mol). 2-Fluoro-benzonitrile (10.37 g, 86 mmol) was then added in portions over 10-15 minutes. The reaction mixture was stirred at room temperature for 12 hours. Upon completion, the mixture was filtered and then concentrated. The residue diluted with water and extracted by dichloromethane. The organic phases were combined, washed by brine, dried over anhydrous sodium sulfate and evaporated to afford the product N-(2-cyanophenyl)-N-methylmethane-sulfonamide (16.0 g, yield 88.9%). 1H NMR (400 MHz, CDCl3) δ ppm 7.62-7.73 (m, 2H), 7.54-7.56 (m, 1H), 7.45-7.50 (m, 1H), 3.40 (s, 3H), 3.14 (s, 3H).

Workup

  1. filtrationUpon completion, the mixture was filtered
  2. concentrationconcentrated
  3. additionThe residue diluted with water
  4. extractionextracted by dichloromethane
  5. washwashed by brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-fa41dcf91c9c49d2b4a57f99eb725d7c
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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