Réaction #1674589

ord-d09103a12bc443c9b1552e7355d49de0

Équation de réaction

COc1ccc(C(=O)C(Cl)c2ccc(OC)cc2)cc1
1,2-bis(4-methoxyphenyl)-2-chloroethanone
NC(=S)N=C(N)N
N-diaminomethylenethiourea
O
water
COc1ccc(-c2nc(NC(=N)N)sc2-c2ccc(OC)cc2)cc1
4,5-bis(4methoxyphenyl)-2-guanidinothiazole
Rendement 53.3%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurewas refluxed for 12 hours
  2. 2
    Extractionextracted with ethyl acetate
  3. 3
    LavageThe separated organic layer was washed with water and brine
  4. 4
    Séchagedried over magnesium sulfate
  5. 5
    Autreevaporated in vacuo
  6. 6
    AutreThe residue was chromatographed n alumina
  7. 7
    Lavageeluting with a mixture of chloroform and methanol
  8. 8
    Concentrationconcentrated in vacuo
  9. 9
    LavageThe residue was washed with isopropy ether

Mode opératoire

A mixture of 1,2-bis(4-methoxyphenyl)-2-chloroethanone (1.00 g) and N-diaminomethylenethiourea (0.65 g) in ethanol (20 ml) was refluxed for 12 hours. After allowing to cool to ambient temperature, then the reaction mixture was poured into water and extracted with ethyl acetate. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed n alumina, eluting with a mixture of chloroform and methanol. The desired fractions were combined and concentrated in vacuo. The residue was washed with isopropy ether to give 4,5-bis(4methoxyphenyl)-2-guanidinothiazole (0.65 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05217971uspto-grants-1993_06