CID 19593658 → HCID 22662731, compound

HRID 392035Notes

Reaction equation

HRID 392035 reaction equation
[CH2:1]([NH:3][S:4]([C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)(=[O:6])=[O:5])[CH3:2].O1CC[CH2:19]OO1>CS(O)(=O)=O.FC(F)(F)C(O)=O>[CH2:1]([N:3]1[CH2:19][C:15]2[C:8]3[C:7](=[CH:11][S:10][C:9]=3[CH:12]=[CH:13][CH:14]=2)[S:4]1(=[O:5])=[O:6])[CH3:2]

Participants

5

Reactant 2

HCID 19593658CID 19593658HCID 22662726HCID 22662726, compound

Product 1

HCID 22662731HCID 22662731, compound

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1.90 g of N-ethyl-benzo[b]thiophene-3-sulphonamide are dissolved in 25 ml methanesulphonic acid at 35° C. and combined with a solution of 0.29 g of trioxane in 8 ml of trifluoroacetic acid. After 2.5 h stirring at ambient temperature the reaction mixture is poured onto 400 ml of ice water. The solid formed is separated off by filtration, washed with 200 ml of water and then dissolved while hot in 400 ml of ethanol/isopropanol (1:1) and separated from solid residues by filtering again. The residue remaining after the concentration of the filtrate is purified by chromatography. Yield: 0.82 g. M.p.: 156° C.

Workup

  1. customThe solid formed
  2. customis separated off by filtration
  3. washwashed with 200 ml of water
  4. dissolutiondissolved while hot in 400 ml of ethanol/isopropanol (1:1)
  5. customseparated from solid residues
  6. filtrationby filtering again
  7. customis purified by chromatography

Sources & evidence

ORD record
ord-41d58fb2aaf44db2b0607d946db65f97
Source dataset
uspto-grants-2004_10
Patent number
US06800623B2

Reaction notes

Loading…