Triethylamine → methyl 3-chloro-4-[N'-(2-chlorophenyl)ureido]phenylacetate

HRID 354376

Reaktionsgleichung

Reaktionsgleichung von HRID 354376
[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].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23].CCN(CC)CC>C1COCC1>[Cl:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:22]([NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14])=[O:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 76833Chlorophenyl isocyanate2×HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Produkt 1

HCID 23512406methyl 3-chloro-4-[N'-(2-chlorophenyl)ureido]phenylacetateAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of methyl 4-amino-3-chlorophenylacetate (1.00 g, 5.01 mmol) and 2-chlorophenyl isocyanate (0.60 ml, 5.01 mmol) in THF (20 ml) was added Et3N (0.14 ml, 1.00 mmol) at room temperature. After 1 day stirring, 2-chlorophenyl isocyanate (0.60 ml, 5.01 mmol) was added to the reaction mixture and stirred 17 h. The reaction mixture was concentrated in vacuo. The residue was triturated by the addition of n-hexane to give methyl 3-chloro-4-[N′-(2-chlorophenyl)ureido]phenylacetate (1.35 g, 76%) as a colorless powder. 1H-NMR (CDCl3) δ3.58 (s, 3H), 3.71 (s, 2H), 7.04 (m, 3H), 7.18 (dd, J=8.5, 2.0 Hz, 1H), 7.27-7.39 (m, 3H), 8.07 (m, 2H); MS (ESI) m/z 353 (M++1), 355 (M++3), 357 (M++5).

Aufarbeitung

  1. stirringstirred 17 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was triturated by the addition of n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-c097c8b9b35247f399ba14bf72666327
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756378B2

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