Trifluoromethanesulfonic acid → HCID 67476460, compound

HRID 1693145Notes

Reaction equation

HRID 1693145 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[CH2:15][S:16][C:17](=[NH:19])[NH2:18].FC(F)(F)S(O)(=O)=O.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.C(OCC)C>[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@:9]12[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[CH2:15][S:16][C:17]([NH2:18])=[N:19]2

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 67279256HCID 67279256, compound

Product 1

HCID 67476460HCID 67476460, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-[2-(2-Fluorophenyl)cyclohex-1-enylmethyl]isothiourea hydrochloride obtained in Preparation Example 1-(5) (6.38 g) was dissolved in TFA (32.0 mL) under ice-cooling, and trifluoromethanesulfonic acid (6.40 mL) was added dropwise at the same temperature. The reaction solution was stirred overnight with gradual warming to room temperature. The reaction solution was poured into ice, diluted with diethyl ether and then neutralized with sodium bicarbonate. The generated reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by NH-silica gel column chromatography to obtain the title compound (4.58 g).

Workup

  1. temperaturecooling
  2. additionThe reaction solution was poured into ice
  3. customThe generated reaction mixture
  4. extractionwas extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customto obtain a crude product
  9. customThe crude product was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-0d00610e56e9450f9e038202e1b41490
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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