Toluene → HCID 69128554, compound

HRID 1918439Notes

Reaction equation

HRID 1918439 reaction equation
C1(NC(=O)C=COC2C=CC=CC=2)C=CC=CC=1.[C:19]1([N:25]=[C:26]([S:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:27]=[CH:28][O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(C)C=CC=CC=1.S(Cl)(Cl)=O>CN(C=O)C.C(N(CC)CC)C>[C:19]1([N:25]=[C:26]([S:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:27]=[CH:28][O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 69128553HCID 69128553, compound

Product 1

HCID 69128554HCID 69128554, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

Phenyl N-phenyl-3-(phenoxy)thioacrylimidate 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-e6690db47f5846b0b53b3af06ba5d725
Source dataset
uspto-grants-2013_12
Patent number
US08618329B2

Reaction notes

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