Trifluoroacetic acid → (E)-2-pyridin-3-yl-ethenesulfonic acid amide

HRID 1272077Notes

Reaction equation

HRID 1272077 reaction equation
CC([NH:9][S:10](/[CH:13]=[CH:14]/[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=[O:12])=[O:11])(C)CC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15](/[CH:14]=[CH:13]/[S:10]([NH2:9])(=[O:11])=[O:12])[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86609961HCID 86609961, compound

Product 1

HCID 14912437(E)-2-pyridin-3-yl-ethenesulfonic acid amideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(E)-2-pyridin-3-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (3.63 g, 12.3 mmol) was stirred for 3 hours in a 1:1 mixture of trifluoroacetic acid and dichloromethane (40 mL). The solvent was concentrated in vacuo to afford a yellow oil. The oil was dissolved in dichloromethane (50 mL) and washed with saturated sodium bicarbonate solution (50 mL), dried over MgSO4, filtered and concentrated in vacuo to afford (E)-2-pyridin-3-yl-ethenesulfonic acid amide as a pale yellow solid (1.65 g, 73%).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customto afford a yellow oil
  3. washwashed with saturated sodium bicarbonate solution (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cd858cc17ea436f81ca3b3d2ee3ddc2
Source dataset
uspto-grants-2007_04
Patent number
US07208506B2

Reaction notes

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