p-Fluorotoluene-alpha-thiol → benzyl 3-(4-fluorobenzylthio)-N-phenyl-thioacrylimidate

HRID 661747Notes

Reaction equation

HRID 661747 reaction equation
[C:1]1([N:7]=[C:8]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]#[CH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][SH:25])=[CH:22][CH:21]=1.CC(C)([O-])C.[K+]>C(Cl)(Cl)Cl>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][S:25][CH:10]=[CH:9][C:8](=[N:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 85171p-Fluorotoluene-alpha-thiolHCID 23665647Potassium tert-butoxideHCID 86617334Benzyl N-phenylpropynthioimidate

Product 1

HCID 86617333benzyl 3-(4-fluorobenzylthio)-N-phenyl-thioacrylimidate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Benzyl N-phenylpropynthioimidate (0.30 g) and 4-fluorobenzylmercaptan were dissolved to chloroform (15 ml), catalytic amount of potassium t-butoxide was added thereto under ice-cooling and stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to obtain benzyl 3-(4-fluorobenzylthio)-N-phenyl-thioacrylimidate (0.15 g) as light yellow oil.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-ceb10f6f62264911a8fb5cbfff922df2
Source dataset
uspto-grants-2011_12
Patent number
US08084644B2

Reaction notes

Loading…