Dimethylformamide → 1115962-75-8

HRID 906916Notes

Reaction equation

HRID 906916 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:13])(=[O:12])N)=[N:6][CH:5]=1.[H-].[Na+].CI.C[N:20]([CH:22]=O)[CH3:21]>>[CH3:22][N:20]([CH3:21])[S:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:14])=[O:2])=[CH:5][N:6]=1)(=[O:12])=[O:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54857421HCID 54857421, compound

Product 1

HCID 548574061115962-75-8Yield 19%

Procedure

1st step: To a stirred solution of 6-sulfamoyl-nicotinic acid methyl ester (250 mg, 1.15 mmol) in DMF (10 mL) at 0° C. was added NaH (53 mg, 55%, 1.20 mmol). After 10 minutes, MeI (0.079 mL, 1.26 mL) was added. Stirring was continued for one hour before the reaction was quenched upon addition of H2O. The product was extracted with EtOAc, the combined organic layers were dried over Na2SO4 and concentrated under vacuo. Column chromatography (SiO2, EtOAc/H, 1/2) afforded 51 mg of the title compound (19%) as a white solid.

Workup

  1. waitwas continued for one hour before the reaction
  2. customwas quenched upon addition of H2O
  3. extractionThe product was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-de6602dd10cd4834b81500f8ec344465
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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