Thiophenol → HCID 19835084, compound

HRID 477873Notes

Reaction equation

HRID 477873 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:15]([S:19][C:20]1[S:21][C:22]([C:26]#[N:27])=[C:23](Cl)[N:24]=1)[CH2:16][CH2:17][CH3:18]>C(#N)C>[CH2:15]([S:19][C:20]1[S:21][C:22]([C:26]#[N:27])=[C:23]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:24]=1)[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 19835036HCID 19835036, compound

Product 1

HCID 19835084HCID 19835084, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.15 ml (5.55 g) of thiophenol and 7.0 ml of triethylamine are added successively while stirring to a solution of 10.93 g of 2-n-butylthio-4-chloro-5-cyanothiazole prepared according to Example V(b), in 100 ml of acetonitrile. After stirring at room temperature for another hour and leaving to stand overnight, the reaction mixture is evaporated. The residue is dissolved in methylene chloride, after which the organic solution is successively washed with water, 1N sodium hydroxide solution and water, and is then dried, filtered and evaporated. Chromatography in petroleum ether (40-60)/diethyl ether 3:1 v/v as a solvent over a 1400 ml dry silica gel column provides the desired product in a yield of 7.24 g; oil; Rf (petr.ether/diethyl ether 3:1 v/v) 0.35; identification by means of I.R. spectrum.

Workup

  1. customprepared
  2. customleaving
  3. customthe reaction mixture is evaporated
  4. dissolutionThe residue is dissolved in methylene chloride
  5. washafter which the organic solution is successively washed with water, 1N sodium hydroxide solution and water
  6. customis then dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-f3b908b146bd4f07acd8a4a7295c8e14
Source dataset
uspto-grants-1989_12
Patent number
US04889863

Reaction notes

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