Thiophenol → HCID 19835105, compound

HRID 477874Notes

Reaction equation

HRID 477874 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS([C:11]1[S:12][C:13]([C:17]#[N:18])=[C:14]([NH2:16])[N:15]=1)=O>C(#N)C>[C:1]1([S:7][C:11]2[S:12][C:13]([C:17]#[N:18])=[C:14]([NH2:16])[N:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 19835132HCID 19835132, compound

Product 1

HCID 19835105HCID 19835105, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15.5 ml (16.5 g) of thiophenol are added to a suspension of 9.35 g of 2-methylsulphinyl-4-amino-5-cyanothiazole, prepared according to example I, in 250 ml of acetonitrile, while stirring. After stirring at room temperature for another 30 minutes and leaving to stand overnight, the mixture is filtered with charcoal, after which the filtrate is evaporated. The residue is taken up in methylene chloride, after which the resulting solution is washed, successively with 2N sodium hydroxide solution and water, dried, filtered and diluted with isopropanol. After evaporating the methylene chloride the desired product crystallises in a yield of 7.62 g; m.p. 176°-18° C.; Rf (CH2Cl2) 0.15.

Workup

  1. customprepared
  2. stirringAfter stirring at room temperature for another 30 minutes
  3. customleaving
  4. filtrationthe mixture is filtered with charcoal
  5. customafter which the filtrate is evaporated
  6. washafter which the resulting solution is washed, successively with 2N sodium hydroxide solution and water
  7. customdried
  8. filtrationfiltered
  9. additiondiluted with isopropanol
  10. customAfter evaporating the methylene chloride the desired product
  11. customcrystallises in a yield of 7.62 g

Sources & evidence

ORD record
ord-a3cb6883f659435cb211d9c0f1990818
Source dataset
uspto-grants-1989_12
Patent number
US04889863

Reaction notes

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