Methanesulfonyl chloride → HCID 54334405, compound

HRID 2396916Notes

Reaction equation

HRID 2396916 reaction equation
[CH2:1]([C:3](=[CH:17][CH3:18])[CH:4]=[CH:5][CH2:6][NH:7][C:8]([C:10]1[CH:11]=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=1)=[O:9])[CH3:2].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH2:17]([C:3](=[CH:1][CH3:2])[CH:4]=[CH:5][CH2:6][NH:7][C:8]([C:10]1[CH:11]=[N:12][C:13]([NH:16][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:14][CH:15]=1)=[O:9])[CH3:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54352395HCID 54352395, compound

Product 1

HCID 54334405HCID 54334405, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of N-(4-ethyl-2,4-hexadien-1-yl)-6-amino-3-pyridinecarboxamide (3.0 g) and methanesulfonyl chloride (1.54 g) in pyridine (25 ml) was stirred at 50° C. for 3 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with 0.5N hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (3% methanol-chloroform) to give N-(4-ethyl-2,4-hexadien-1-yl)-6-methansulfonamido-3-pyridinecarboxamide.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 0.5N hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (3% methanol-chloroform)

Sources & evidence

ORD record
ord-07bcfa5d29fc4b1f88b1e0a63ae5badd
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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