2-Amino-6-methylpyridine → 1-Amino-6-methylpyridin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonate

HRID 1771984Notes

Reaction equation

HRID 1771984 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=1>C(Cl)Cl>[NH2:13][N:17]1[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:16]1=[NH2+:15].[CH3:8][C:3]1[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:14])[C:2]=1[S:9]([O-:12])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 157652-Amino-6-methylpyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 1784259731-Amino-6-methylpyridin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of O-(mesitylsulfonyl)hydroxylamine (6.45 g, 30.0 mmol) in DCM (30 mL) was stirred at room temperature, then 2-amino-6-methylpyridine (1.08 g, 10.0 mmol) was added slowly. The reaction mixture was stirred at room temperature for 12 h, and filtered to remove the solvent. A yellow solid was collected which was used for the next step without further purification. ESI MS: m/z 124 [M+H]+.

Workup

  1. filtrationfiltered
  2. customto remove the solvent
  3. customA yellow solid was collected which
  4. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-0589332a74d74baf838def5772df0045
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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