Diisopropylethylamine → Ethyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetate

HRID 1900901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900901
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH2:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=1.[C:26]([C:28]1[CH:38]=[CH:37][C:31]([C:32]([N:34]=[C:35]=[O:36])=[O:33])=[CH:30][CH:29]=1)#[N:27].C(N(C(C)C)CC)(C)C>C(#N)C>[C:26]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([NH:34][C:35](=[O:36])[NH:12][C:13]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=2)=[O:33])=[CH:37][CH:38]=1)#[N:27]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 85570p-ToluenesulfonateHCID 412616Ethyl 2-(4-aminophenoxy)acetateHCID 149137394-Cyanobenzoyl isocyanate

Produkt 1

HCID 23370001Ethyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetateAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Example 1, starting material step (a), the p-toluenesulphonate salt of ethyl 4-aminophenoxyacetate (12.9 g, preparation described by Coutts, I. G. C. et al (1985), J. Chem. Soc. Perkin I, 1829), 4-cyanobenzoyl isocyanate (5.9 g), acetonitrile (400 ml total) and diisopropylethylamine (6.5 ml) were reacted to give, after stirring at ambient temperature for 1.5 hours, a solid, which was crystallised from acetonitrile/ethanol to give ethyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetate (10.16 g) as an off-white solid: m.p. 200°-203° C.; NMR Spectrum (DMSO-d6) 1.22 (3H, t), 4.17 (2H, q), 4.75 (2H, s), 6.93 (2H, d), 7.49 (2H, d), 8.02 (2H, d), 8.13 (2H, d), 10.49 (1H, br s), 11.17 (1H, br s); Mass Spectrum m/Z 368 (M+H)+.

Aufarbeitung

  1. customto give
  2. customa solid, which was crystallised from acetonitrile/ethanol

Quellen und Nachweise

ORD-Eintrag
ord-31cb23665f4644a4987cbe1b01a7c53a
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576334

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