Diisopropylethylamine → t-Butyl 4-[3-(4-cyanobenzoyl)ureido]-3-methylphenoxyacetate

HRID 1900894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900894
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C:13]1[CH:27]=[CH:26][C:16]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:15][C:14]=1[CH3:28].[C:29]([C:31]1[CH:41]=[CH:40][C:34]([C:35]([N:37]=[C:38]=[O:39])=[O:36])=[CH:33][CH:32]=1)#[N:30].C(N(C(C)C)CC)(C)C>C(#N)C>[C:29]([C:31]1[CH:32]=[CH:33][C:34]([C:35]([NH:37][C:38](=[O:39])[NH:12][C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])=[CH:15][C:14]=2[CH3:28])=[O:36])=[CH:40][CH:41]=1)#[N:30]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 149137394-Cyanobenzoyl isocyanateHCID 131719653t-Butyl 4-amino-3-methylphenoxyacetate, p-toluenesulphonate salt

Produkt 1

HCID 23370039t-Butyl 4-[3-(4-cyanobenzoyl)ureido]-3-methylphenoxyacetateAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Example 1, starting material step (a), the product of step (b) (2.9 g), 4-cyanobenzoyl isocyanate (1.23 g), diisopropylethylamine (1.23 ml) and acetonitrile (125 ml total) were reacted to give, after stirring at ambient temperature overnight, a solid, which was crystallised from acetonitrile/ether to give t-butyl 4-[3-(4-cyanobenzoyl)ureido]-3-methylphenoxyacetate (611 mg) as an off-white solid: NMR Spectrum (DMSO-d6) 1.44 (9H, s), 2.27 (3H, s), 4.61 (2H, s), 6.73 (1H, dd), 6.81 (1H, d), 7.72 (1H, d), 8.00 (2H, d), 8.13 (2H, d), 10.41 (1H, s), 11.23 (1H, s); Mass Spectrum m/Z 432 (M+Na)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-aee4236aeea2478c91e16612edad9b6e
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576334

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