Potassium Carbonate → HCID 66980874, compound

HRID 910759Notes

Reaction equation

HRID 910759 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:10][S:11]([CH3:14])(=[O:13])=[O:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:4]([C:3]1[C:2]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[N:9][CH:8]=[CH:7][CH:6]=1)#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 810792-Chloronicotinonitrile

Product 1

HCID 66980874HCID 66980874, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-nicotinonitrile (2 g), H2NSO2Me (1.73 g) and K2CO3 (4.44 g) in DMF (100 ml) was stirred at 100° C. for 18 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water and brine. The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel in dichloromethane/methanol=98/2 (v/v) as eluent. Yield: 1.32 g. MS-ESI: [M+H]+=198.2

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel in dichloromethane/methanol=98/2 (v/v) as eluent

Sources & evidence

ORD record
ord-6940f107b68c480e99b7e2dde5f518d9
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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