m-Toluidine → HCID 69128102, compound

HRID 661757Notes

Reaction equation

HRID 661757 reaction equation
C1COCC1.[C:6]1([S:12][CH:13]=[CH:14][C:15](Cl)=[O:16])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22]>C(N(CC)CC)C>[CH3:18][C:19]1[CH:20]=[C:21]([NH:22][C:15](=[O:16])[CH:14]=[CH:13][S:12][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 8028Tetrahydrofuran2×HCID 713526793-(Phenylsulfanyl)prop-2-enoyl chloride

Product 1

HCID 69128102HCID 69128102, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

THF (45 ml) solution of 3-(phenylthio)acryloyl chloride (3.03 g) was added to THF (45 ml) solution of triethylamine (2.09 ml) under ice-cooling. 3-methylaniline (1.62 g) was added to the mixture under ice-cooling and stirred at room temperature for ten hours. The reaction solution was concentrated under reduced pressure. Ice cooled 1N hydrochloric acid (40 ml) and ethyl acetate (200 ml) were added to the residue and separated to two layer. The organic layer was washed with aqueous saturated sodium chloride solution (40 ml) twice, dried over anhydrous magnesium sulfate, filtered off inorganic salt and concentrated under reduced pressure to obtain N-(3-methylphenyl)-3-(phenylthio)acrylamide (3.46 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. temperatureIce cooled 1N hydrochloric acid (40 ml) and ethyl acetate (200 ml)
  5. additionwere added to the residue
  6. customseparated to two layer
  7. washThe organic layer was washed with aqueous saturated sodium chloride solution (40 ml) twice
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered off inorganic salt
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8ca7d5e3289449387c17b3ba7c4bd46
Source dataset
uspto-grants-2011_12
Patent number
US08084644B2

Reaction notes

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