Thiophenol → HCID 69128191, compound

HRID 661750Notes

Reaction equation

HRID 661750 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7](=O)[CH:8]=[CH:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5])[CH3:2].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Na].[C:43]1([SH:49])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>COC(C)(C)C.CN(C=O)C.C(#N)C>[CH2:1]([O:3][C:4]([N:6]=[C:7]([S:49][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH:8]=[CH:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

9

Reactant 5

HCID 7969ThiophenolHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5360545SodiumHCID 69128190HCID 69128190, compound

Product 1

HCID 69128191HCID 69128191, compoundYield 24.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

N-ethoxycarbonyl-3-(phenylthio)acrylamide (1.20 g) was dissolved to acetonitrile (30 ml), then carbon tetrabromide (2.83 g) and triphenylphosphine (2.23 g) was added thereto and heat refluxing for three hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate 20:1) to obtain light yellow oil. It was dissolved to DMF (10 ml), then sodium salt of thiophenol (0.63 g) was added thereto under ice cooling and stirred at room temperature for two hours. t-Butyl methyl ether (100 ml) was added to the reaction mixture, washed successively with 1N aqueous sodium hydroxide solution, water and aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered off inorganic salt and concentrated under reduced pressure. The residue was purified by medium pressure preparative high performance liquid chromatography to obtain phenyl N-ethoxycarbonyl-3-(phenylthio)thioacrylimidate (0.40 g) as light yellow oil.

Workup

  1. temperatureheat
  2. temperaturerefluxing for three hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto obtain light yellow oil
  5. washwashed successively with 1N aqueous sodium hydroxide solution, water and aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered off inorganic salt
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by medium pressure preparative high performance liquid chromatography

Sources & evidence

ORD record
ord-680c2939cabd4246bddcdd928503d156
Source dataset
uspto-grants-2011_12
Patent number
US08084644B2

Reaction notes

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