Toluene → HCID 69128554, compound

HRID 661733Notes

Reaction equation

HRID 661733 reaction equation
[C:1]1([NH:7][C:8](=O)[CH:9]=[CH:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]1(C)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[S:26](Cl)(Cl)=O>CN(C=O)C.C(N(CC)CC)C>[C:1]1([N:7]=[C:8]([S:26][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=[CH:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 69127057HCID 69127057, compound

Product 1

HCID 69128554HCID 69128554, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

N-phenyl-3-phenoxyacrylamide (1.5 g) was suspended to toluene (80 ml), then thionyl chloride (0.82 ml), triethylamine (1.8 ml) and one drop of DMF were added thereto at room temperature. The mixture was stirred on the 60° C. oil bath for three hours. Then it was cooled and filtered off the insoluble matter. The filtrate was concentrated under reduced pressure. The residue was dissolved to DMF (80 ml). Sodium salt of thiophenol (0.82 g) was added to it under ice-cooling, and stirred for 2 hours. t-Butyl methyl ether (250 ml) was added to the reaction mixture. It was successively washed with 1N aqueous sodium hydroxide solution, water and aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered off an inorganic salt, concentrated under reduced pressure. The residue was isolated and purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain phenyl N-phenyl-3-(phenoxy)thioacrylimidate (0.28 g) as yellow oil.

Workup

  1. customat room temperature
  2. temperatureThen it was cooled
  3. filtrationfiltered off the insoluble matter
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved to DMF (80 ml)
  6. additionSodium salt of thiophenol (0.82 g) was added to it under ice-
  7. temperaturecooling
  8. stirringstirred for 2 hours
  9. additiont-Butyl methyl ether (250 ml) was added to the reaction mixture
  10. washIt was successively washed with 1N aqueous sodium hydroxide solution, water and aqueous saturated sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered off an inorganic salt
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was isolated
  15. custompurified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-844d5f25db024a989f91302f8f743ba5
Source dataset
uspto-grants-2011_12
Patent number
US08084644B2

Reaction notes

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