Water → ethyl 3-[N'-(2-bromophenyl)ureido]-2-methoxy-6-pyridylacetate

HRID 350409

Reaktionsgleichung

Reaktionsgleichung von HRID 350409
[NH2:1][C:2]1[C:3]([O:14][CH3:15])=[N:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]=[C:24]=[O:25].O>C1COCC1>[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24](=[O:25])[NH:1][C:2]1[C:3]([O:14][CH3:15])=[N:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 1370972-Bromophenyl isocyanateHCID 69334098Ethyl 3-amino-2-methoxy-6-pyridylacetate

Produkt 1

HCID 69333268ethyl 3-[N'-(2-bromophenyl)ureido]-2-methoxy-6-pyridylacetateAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 3-amino-2-methoxy-6-pyridylacetate (1.61 g, 7.66 mmol) in THF (10 ml) were added 2-bromophenylisocyanate (948 ml, 7.66 mmol) and Et3 N (107 ml, 0.776 mmol). After stirring overnight, the mixture was poured into H2O (100 ml) and extracted with CHCl3-MeOH (4:1, 2×200 ml). The combined extracts were dried over MgSO4 and evaporated. The residue was recrystallized from CHCl3-MeOH-hexane to give ethyl 3-[N′-(2-bromophenyl)ureido]-2-methoxy-6-pyridylacetate (2.91 g, 93%) as a colorless crystalline powder. mp 160–163° C.; 1H-NMR (DMSO-d6) δ 1.19 (dt, J=7.1, 0.7 Hz, 3 H), 3.69 (s, 2 H), 3.95 (s, 3 H), 4.07–4.13 (m, 2 H), 6.90 (d, J=7.8 Hz, 1 H), 6.99 (t, J=7.8 Hz, 1 H), 7.33 (t, J=7.8 Hz, 1 H), 7.61 (d, J=7.8 Hz, 1 H), 7.96 (dd, J=7.8, 1.5 Hz, 1 H), 8.31 (d, J=7.8 Hz, 1 H), 8.82 (s, 1 H), 9.12 (s, 1 H); MS (FAB) m/z 408 (M+), 410 (M++2); Anal. Calcd for C17H18BrN3O4.0.25 H2O: C, 49.47; H, 4.52; 9.96. Found: C, 49.34; H, 4.48; N, 9.96.

Aufarbeitung

  1. extractionextracted with CHCl3-MeOH (4:1, 2×200 ml)
  2. dry with materialThe combined extracts were dried over MgSO4
  3. customevaporated
  4. customThe residue was recrystallized from CHCl3-MeOH-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ea157780ba05440c85acfde2ec47048b
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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