2-Bromophenyl isocyanate → methyl 4-[N'-(2-bromophenyl)ureido]-3-chlorophenylacetate

HRID 350442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350442
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[Cl:13].[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23]>C1COCC1>[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22](=[O:23])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[Cl:13]

Komponenten

4

Edukt 2

HCID 1370972-Bromophenyl isocyanate2×HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Produkt 1

HCID 23512063methyl 4-[N'-(2-bromophenyl)ureido]-3-chlorophenylacetateAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of methyl 4-amino-3-chlorophenylacetate (1.00 g, 5.01 mmol) and 2-bromophenyl isocyanate (0.62 ml, 5.01 mmol) in THF (20 ml) was added Et3 N (0.14 ml, 1.00 mmol) at room temperature. After 1 day stirring, 2-bromophenyl isocyanate (0.60 ml, 5.01 mmol) was added to the reaction mixture and stirred 24 h. The reaction mixture was concentrated in vacuo. The residue was triturated by the addition of n-hexane to give methyl 4-[N′-(2-bromophenyl)ureido]-3-chlorophenylacetate (1.34 g, 67%) as a colorless powder. 1H-NMR (CDCl3) δ 3.58 (s, 3H), 3.70 (s, 2H), 6.98 (m, 3H), 7.19 (dd, J=8.3, 1.9 Hz, 1H), 7.32 (m, 1H), 7.51 (m, 2H), 8:05 (m, 1H); MS (ESI) m/z 398 (M++1), 400 (M++3), 402 (M++5).

Aufarbeitung

  1. additionwas added Et3 N (0.14 ml, 1.00 mmol) at room temperature
  2. stirringstirred 24 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe residue was triturated by the addition of n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ba847e7aa48f44d4a81eb67962bb43d2
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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