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p-Toluenesulfonic acid monohydrate → Isopropyl 2-chloro-4-fluoro-5-{3-[2-(methoxycarbonyl)propenyl]ureido}-benzoate

HRID 1252970
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1252970
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([NH:15][C:16]([NH2:18])=[O:17])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].CO[CH:21]=[C:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([NH:15][C:16]([NH:18][CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[CH3:27])=[O:17])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5]
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Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 3019052Methyl 3-methoxy-2-methyl-acrylateHCID 20130672Isopropyl 2-chloro-4-fluoro-5-ureidobenzoate

Produkt 1

HCID 54564066Isopropyl 2-chloro-4-fluoro-5-{3-[2-(methoxycarbonyl)propenyl]ureido}-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

27.4 g of isopropyl 2-chloro-4-fluoro-5-ureidobenzoate and 13.0 g of methyl 3-methoxy-2-methyl-acrylate are heated under reflux for 2 hours in 250 ml of benzene with 1.9 g of toluene-4-sulphonic acid monohydrate. The reaction mixture is evaporated to dryness under reduced pressure and the residue is stirred with 400 ml of diethyl ether. The insoluble material is filtered off under suction and the filtrate is evaporated to dryness under reduced pressure. The residue is purified by chromatography on 1 kg of silica gel using ethyl acetate/n-hexane (1:3) as the eluent. There is obtained isopropyl 2-chloro-4-fluoro-5-{3-[2-(methoxycarbonyl)propenyl]ureido}-benzoate, m.p. 189°-190° C.

Aufarbeitung

  1. customThe reaction mixture is evaporated to dryness under reduced pressure
  2. filtrationThe insoluble material is filtered off under suction
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. customThe residue is purified by chromatography on 1 kg of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9f6c3169fb534556aaa091a80ef5c8e2
Quelldatensatz
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04746352

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