Trifluoroacetic acid → 5-(Ethylsulfonyl)pyridin-2-amine

HRID 1817871Notes

Reaction equation

HRID 1817871 reaction equation
C(S[C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)C.F[C:12](F)(F)[C:13](O)=O.ClC1C=CC=C(C(OO)=O)C=1.[S:29]([O-:32])([O-])=[O:30].[Na+].[Na+]>ClCCl>[CH2:12]([S:29]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)(=[O:32])=[O:30])[CH3:13]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 115211175-(Ethylthio)pyridin-2-amine

Product 1

HCID 284117055-(Ethylsulfonyl)pyridin-2-amineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(ethylthio)pyridin-2-amine (Step A, 1.23 g, 7.96 mmol) in dichloromethane (30 mL) were added trifluoroacetic acid (1.2 mL, 15.9 mmol) and m-chloroperbenzoic acid (4.3 g, 17.5 mmol) at 0° C. The mixture was stirred at 0° C. for 2 h. Aqueous sodium sulfite (20 mL) was added. The mixture was extracted with dichloromethane (30 mL×3) and washed with aqueous sodium hydrogencarbonate (15 mL×2). The organic extracts were dried over sodium sulfate and concentrated to afford the title compound (1.43 g, 97%) as a white solid.

Workup

  1. extractionThe mixture was extracted with dichloromethane (30 mL×3)
  2. washwashed with aqueous sodium hydrogencarbonate (15 mL×2)
  3. dry with materialThe organic extracts were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4db708d1222b4f22bdc08c63d1e81ffa
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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