Potassium Carbonate → HCID 58579786, compound

HRID 661752Notes

Reaction equation

HRID 661752 reaction equation
[C:1]1([N:7]=[C:8]([S:15][CH2:16][CH:17]2[CH2:19][CH2:18]2)[C:9]#[C:10][Si](C)(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[F:26][C:27]1[CH:32]=[CH:31][C:30]([SH:33])=[CH:29][CH:28]=1>CO>[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33][CH:10]=[CH:9][C:8](=[N:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:15][CH2:16][CH:17]2[CH2:19][CH2:18]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677894-FluorothiophenolHCID 58579770HCID 58579770, compound

Product 1

HCID 58579786HCID 58579786, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopropylmethyl N-phenyl-3-(trimethylsilyl)thiopropynimidate (0.91 g) was dissolved in methanol (15 mL), a small amount of potassium carbonate was dissolved thereto at room temperature, and the mixture was stirred for 1 hour. 4-fluorothiophenol (0.35 mL) was added thereto and further stirred for 5.5 hours. The reaction mixture was concentrated under reduced pressure, then the residue was subjected to silica gel column chromatography (hexane/ethyl acetate=20/1), medium pressure HPLC(hexane/ethyl acetate=99.2/0.8-98.5/1.5) to obtain cyclopropylmethyl 3-(4-fluorophenylthio)-N-(phenyl)thioacrylimidate (0.84 g).

Workup

  1. stirringfurther stirred for 5.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-59035def2239490388e43780d984b166
Source dataset
uspto-grants-2011_12
Patent number
US08084644B2

Reaction notes

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