Acetonitrile → 3-n-Butylureido-1-(p-sulfophenyl)-5-pyrazolone Triethylamine Salt

HRID 1449077

Reaktionsgleichung

Reaktionsgleichung von HRID 1449077
[C:1](#[N:3])[CH3:2].[C:4](OOC(CC)(N)C)(=[O:7])[CH:5]=C.[CH2:15]([N:19]=[C:20]=[O:21])[CH2:16][CH2:17][CH3:18].[S:22]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][NH2:33])=[CH:28][CH:27]=1)([OH:25])(=[O:24])=[O:23]>C(O)(=O)C.C(N(CC)CC)C.CO>[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][CH3:5])[CH3:2].[CH2:15]([NH:19][C:20](=[O:21])[NH:3][C:1]1[NH:33][N:32]([C:29]2[CH:28]=[CH:27][C:26]([S:22]([OH:25])(=[O:23])=[O:24])=[CH:31][CH:30]=2)[C:4](=[O:7])[CH:2]=1)[CH2:16][CH2:17][CH3:18]

Komponenten

8

Edukt 4

HCID 6342AcetonitrileHCID 8110Butyl isocyanateHCID 668254-Hydrazinobenzenesulfonic acidHCID 86736826Ethylbeta-amino-beta-ethoxy acrylate

Produkt 1

HCID 867368333-n-Butylureido-1-(p-sulfophenyl)-5-pyrazolone Triethylamine Salt

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Into 30 ml of acetonitrile were dissolved 15.9 g of ethylβ-amino-β-ethoxy acrylate and 10 g of n-butyl isocyanate, and the system then allowed to stand at room temperature for 3 days. Into a mixed solution of 50 ml of methanol. 50 ml of triethylamine and 50 ml of glacial acetic acid was dissolved 18.8 g of p-sulfophenyl hydrazine, to which was slowly added the above ester reaction solution. The resulting solution was allowed to stand at room temperature for 7 days and then concentrated under reduced pressure. The concentrated residue was dissolved by adding 50 ml of ethanol containing 35% by wt. hydrogen chloride thereto. On standing the solution so obtained in a refrigerator for one night, crystals precipitated. The crystals were collected and recrystallized from ethanol, whereupon 26.5 g of needle-like crystals of the objective compound of a melting point of 174° to 176° C. was obtained.

Aufarbeitung

  1. additionto which was slowly added
  2. waitto stand at room temperature for 7 days
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe concentrated residue was dissolved
  5. additionby adding 50 ml of ethanol containing 35% by wt. hydrogen chloride
  6. customso obtained in a refrigerator for one night
  7. customcrystals precipitated
  8. customThe crystals were collected
  9. customrecrystallized from ethanol, whereupon 26.5 g of needle-like crystals of the objective compound of a melting point of 174° to 176° C.
  10. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-75dc2a636bc04272a9ef3408ed514f6d
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04188489

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