Dimethylformamide → HCID 69128432, compound

HRID 1918447Notes

Reaction equation

HRID 1918447 reaction equation
CN(C=O)C.[C:6]1([N:12]=[C:13]([O:23][C:24]2[CH:29]=CC=CC=2)[CH:14]=[CH:15]OC2C=CC=CC=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Na].[CH2:31]([SH:33])[CH3:32]>C(OCC)(=O)C>[C:6]1([N:12]=[C:13]([O:23][CH2:24][CH3:29])[CH:14]=[CH:15][S:33][CH2:31][CH3:32])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 5360545SodiumHCID 69127142Phenyl 3-phenoxy-N-phenylacrylimidate

Product 1

HCID 69128432HCID 69128432, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To DMF (5 ml) solution of phenyl N-phenyl-3-phenoxyacrylimidate (0.30 g) was added sodium salt of ethyl mercaptan (0.10 g) under ice-cooling, and stirred for three hours at the same temperature. Ethyl acetate (80 ml) was added to the reaction solution, and it was successively washed with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. DMF (5 ml) and sodium salt of ethyl mercaptan (0.1 g) were added to the residue, and stirred for three hours at room temperature. Ethyl acetate (80 ml) was added to the reaction solution and it was successively washed with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was isolated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain ethyl N-phenyl-3-(ethylthio)acrylimidate (0.14 g) as yellow oil.

Workup

  1. temperaturecooling
  2. washwas successively washed with water and aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionDMF (5 ml) and sodium salt of ethyl mercaptan (0.1 g) were added to the residue
  6. stirringstirred for three hours at room temperature
  7. additionEthyl acetate (80 ml) was added to the reaction solution and it
  8. washwas successively washed with water and aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was isolated
  12. custompurified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-e264912e35534a8b95c266395e430c0a
Source dataset
uspto-grants-2013_12
Patent number
US08618329B2

Reaction notes

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