4-Fluorothiophenol → HCID 58579766, compound

HRID 1918460Notes

Reaction equation

HRID 1918460 reaction equation
[C:1]1([N:7]=[C:8]([S:11][CH:12]([CH2:18][CH3:19])[CH:13]([CH3:17])[CH2:14][CH2:15][CH3:16])[C:9]#[CH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=1>C(Cl)(Cl)Cl>[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27][CH:10]=[CH:9][C:8](=[N:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:11][CH:12]([CH2:18][CH3:19])[CH:13]([CH3:17])[CH2:14][CH2:15][CH3:16])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 677894-FluorothiophenolHCID 58579818HCID 58579818, compound

Product 1

HCID 58579766HCID 58579766, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1-ethyl-2-methylpentyl N-phenylpropynthioimidate (0.44 g) was dissolved to chloroform (8 mL), chloroform (3 mL) solution of 4-fluorothiophenol (0.16 g) was added to the solution under ice-cooling, and then it was stirred for 18 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to medium pressure HPLC (hexane/ethyl acetate=98/2) to obtain 1-ethyl-2-methylpentyl 3-(4-fluorophenylthio)-N-(phenyl)thioacrylimidate (0.28 g) as pale yellow oil.

Workup

  1. additionwas added to the solution under ice-
  2. temperaturecooling
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-347360e8b6e04e6da84b47f413038af7
Source dataset
uspto-grants-2013_12
Patent number
US08618329B2

Reaction notes

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