Pyridine → HCID 178482231, compound

HRID 1722926Notes

Reaction equation

HRID 1722926 reaction equation
N1C=CC=C[CH:2]=1.C([N:10]1[C:14]([NH2:15])=[N:13][C:12]([S:16]([NH:19][C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])(=[O:18])=[O:17])=[N:11]1)(=O)C.[H-].[Na+].CI>CN(C)C=O>[NH2:15][C:14]1[NH:10][N:11]=[C:12]([S:16]([N:19]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])[CH3:2])(=[O:18])=[O:17])[N:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14255125HCID 14255125, compound

Product 1

HCID 178482231HCID 178482231, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.80 g (22.8 mmol) of the pyridine salt of 1-acetyl-5-amino-N-(2,6-dichlorophenyl)-1,2,4-triazole-3-sulphonamide was dissolved in 300 ml dimethylformamide and 0.89 g (29.7 mmol) 80% sodium hydride added portionwise at room temperature. The mixture was stirred for a further 30 minutes and 1.7 ml (27.8 mmol) methyl iodide added. The mixture was allowed to stand overnight and concentrated. The residue was taken up in 2N aqueous sodium hydroxide and made slightly acidic by addition of 3N hydrochloric acid. The crystals were separated, washed with water and ether and recrystallised from acetonitrile.

Workup

  1. waitto stand overnight
  2. concentrationconcentrated
  3. additionmade slightly acidic by addition of 3N hydrochloric acid
  4. customThe crystals were separated
  5. washwashed with water and ether
  6. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-f1c2d3df88ca479f8bd15ff87b4cc385
Source dataset
uspto-grants-1989_08
Patent number
US04859231

Reaction notes

Loading…