Trimethyl orthoformate → N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonylmethylurea

HRID 1111053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1111053
[CH2:1]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH:2]=[CH2:3].[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1)=O.Cl.[NH2:22][OH:23].C(OC)(OC)OC>C1COCC1.N1C=CC=CC=1>[OH:23][N:22]=[C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:7][CH2:6][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:8])=[O:20])=[CH:14][CH:13]=1)[CH3:9]

Komponenten

7

Edukt 4

HCID 9005Trimethyl orthoformateHCID 994524-Acetylphenyl isocyanateHCID 108831Allyl glycinateHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 131716732N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonylmethylurea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.02 mol glycine allyl ester in 40 mL of THF is added dropwise to a solution of 0.02 mol of 4-isocyanatoacetophenone and 5 mL of pyridine in 40 mL of THF and the reaction mixture is stirred for 3 hours. The solvent is then removed by rotary evaporator. The residue is dispersed in 50 mL of CH3OH, and 0.022 mol of hydroxylamine hydrochloride and 0.06 mol of trimethyl orthoformate are added. The reaction mixture is heated to reflux for 1 hour. The solvent is removed by rotary evaporator to give the product, N-[4-(1-hydroxyiminoethyl)phenyl]-N'-allyloxycarbonylmethylurea.

Aufarbeitung

  1. customThe solvent is then removed by rotary evaporator
  2. additionThe residue is dispersed in 50 mL of CH3OH
  3. temperatureThe reaction mixture is heated
  4. temperatureto reflux for 1 hour
  5. customThe solvent is removed by rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-2b73cd12e7f6451c8e70c0932770b2ce
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04977272

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