2-Pyridinamine, N-methyl- → HCID 112686069, compound

HRID 1054454Notes

Reaction equation

HRID 1054454 reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[S:11](Cl)(=[O:14])(=[O:13])[NH2:12]>C1COCC1>[CH3:3][N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[S:11]([NH2:12])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 207272-Pyridinamine, N-methyl-HCID 24499Chlorosulfamic acidHCID 24758Sodium hydride

Product 1

HCID 112686069HCID 112686069, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of NaH (60%) (0.112 g, 2.78 mmol) in THF (6 ml), N-methylpyridin-2-amine (prepared by N-methylation of 2-aminopyridine) (0.3 g, 2.78 mmol) in THF (2 ml) was added and stirred for 1 h. To this a solution of Sulfamoyl chloride (0.32 g, 2.78 mmol) in THF (1 ml) was added and stirred for 2 h at RT. Reaction mass was quenched with methanol (0.6 ml) at ice cold condition and concentrated to dryness to get crude which was purified using neutral alumina column, eluent ethyl acetate in n-Hexane 0 to 85% to afford N-methyl-N-(pyridin-2-yl)sulfamide as off white solid (0.12 g, 23% yield)

Workup

  1. stirringstirred for 2 h at RT
  2. customReaction mass
  3. customwas quenched with methanol (0.6 ml) at ice cold condition
  4. concentrationconcentrated to dryness
  5. customto get crude which
  6. customwas purified

Sources & evidence

ORD record
ord-dd9243b3c3de4b0ab56d915a9c1c27a7
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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