creatinine → 1-(5-Bromo-2-thienyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) urea

HRID 904169

Reaktionsgleichung

Reaktionsgleichung von HRID 904169
[CH3:1][N:2]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[CH2:3]1.[Br:9][C:10]1[S:14][C:13]([N:15]=[C:16]=[O:17])=[CH:12][CH:11]=1.O>CN(C=O)C.C1(C)C=CC=CC=1>[Br:9][C:10]1[S:14][C:13]([NH:15][C:16]([N:8]=[C:7]2[NH:6][C:4](=[O:5])[CH2:3][N:2]2[CH3:1])=[O:17])=[CH:12][CH:11]=1

Komponenten

6

Edukt 3

HCID 588creatinineHCID 962WaterHCID 233337742-Bromo-5-isocyanatothiophene

Produkt 1

HCID 1359973341-(5-Bromo-2-thienyl)-3-(tetrahydro-1-methyl-4-oxo-1H-imidazol-2-ylidene) ureaAusbeute 29,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a stirred suspension of 3.0 g (26 mM) of creatinine in 30 ml of anhydrous DMF was added a solution of 5.0 g (26.5 mM) of 5-bromo-2-thienyl isocyanate in 15 ml of toluene. The resulting mixture was heated at 75° C. for 3 hrs., cooled, and poured into 200 ml of water. The precipitate was collected, washed with ethanol and ether, and air-dried. The solid was dissolved in 250 ml hot acetone, treated with charcoal, filtered, and the filtrate diluted with water (250 ml). The resulting precipitate was collected, washed with acetone and then ether. Air-drying gave 2.3 g of the above urea as a buff powder, m.p. 192°-193° C. (dec.).

Aufarbeitung

  1. temperature, cooled
  2. customThe precipitate was collected
  3. washwashed with ethanol and ether
  4. customair-dried
  5. dissolutionThe solid was dissolved in 250 ml hot acetone
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. additionthe filtrate diluted with water (250 ml)
  9. customThe resulting precipitate was collected
  10. washwashed with acetone
  11. customAir-drying

Quellen und Nachweise

ORD-Eintrag
ord-fbcc51154ef34c1090a8298350c4eede
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04230713

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