p-Chlorothiophenol → HCID 86617326, compound

HRID 1918448Notes

Reaction equation

HRID 1918448 reaction equation
[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3](=[N:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]#[CH:5].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1>C(Cl)(Cl)Cl>[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3](=[N:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH:4]=[CH:5][S:26][C:23]1[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 7815p-ChlorothiophenolHCID 12272571HCID 12272571, compound

Product 1

HCID 86617326HCID 86617326, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-methyl-N-phenyl-N′-phenylpropynamidine (0.23 g) was dissolved to chloroform (5 ml), chloroform (5 ml) solution of 4-chlorothiophenol (0.14 g) was added dropwise under ice-cooling and stirred for 14 hours at room temperature. The reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1) to obtain N-methyl-N-phenyl-N′-phenyl-3-(4-chlorophenylthio)acrylamidine (0.22 g) as light yellow oil.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-da46f20203614435bd08b174b057b8ed
Source dataset
uspto-grants-2013_12
Patent number
US08618329B2

Reaction notes

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