4-(Trifluoromethyl)pyridine → 1-Amino-4-trifluoromethylpyridinium 2,4,6-trimethylbenzenesulfonate

HRID 1887012Notes

Reaction equation

HRID 1887012 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[C:11]1([CH3:24])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[S:19]([O:22][NH2:23])(=[O:21])=[O:20]>C(Cl)Cl>[CH3:18][C:13]1[CH:14]=[C:15]([CH3:17])[CH:16]=[C:11]([CH3:24])[C:12]=1[S:19]([O-:22])(=[O:21])=[O:20].[NH2:23][N+:6]1[CH:7]=[CH:8][C:3]([C:2]([F:10])([F:9])[F:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 1380554-(Trifluoromethyl)pyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 866713661-Amino-4-trifluoromethylpyridinium 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-trifluoromethylpyridine (2.23 g, 15.2 mmol) in CH2Cl2 (66 ml.) at 0° C., O-(mesitylsulfonyl)hydroxylamine (3.27 g, 15.2 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was filtered to afford the desired product with quantitative yield.

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-29588ff847f84d488ae32a5eec9814fb
Source dataset
uspto-grants-2013_08
Patent number
US08501735B2

Reaction notes

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