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Malonic Acid → 2-(3-Cyclohexyl-2,4,6-trioxotetrahydropyrimidin-1(2H)-yl)benzene-1-sulfonyl fluoride

HRID 441700
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 441700
[CH:1]1([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([F:20])(=[O:19])=[O:18])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21](O)(=[O:26])[CH2:22][C:23](O)=[O:24].C(Cl)(=O)C>O>[CH:1]1([N:7]2[C:21](=[O:26])[CH2:22][C:23](=[O:24])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:17]([F:20])(=[O:19])=[O:18])[C:8]2=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
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Komponenten

5

Edukt 3

HCID 867Malonic AcidHCID 6367Acetyl chloride2×HCID 214172322-[(Cyclohexylcarbamoyl)amino]benzene-1-sulfonyl fluoride

Produkt 1

HCID 214172312-(3-Cyclohexyl-2,4,6-trioxotetrahydropyrimidin-1(2H)-yl)benzene-1-sulfonyl fluoride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of N-cyclohexyl-N'-(2-fluorosulphonylphenyl) urea (300 g, 1 mole), malonic acid (156 g, 1 mole) and acetylchloride (427 ml, 6 moles) was refluxed for 4 hours with stirring, cooled to room temperature, poured into water (4.25 l) and stirred for 1 hour to decompose the excess of acetylchloride. Then the 1-cyclohexyl-3-(2-fluorosulphonylphenyl)barbituric acid formed was added with portions and with stirring to 1N ammoniumhydroxide (5 l, 5 moles). After the last addition, stirring was continued for still an hour. Some insoluble material was filtered off and the filtrate was carefully acidified with 6N sulphuric acid (835 ml) whilst cooling by the addition of crushed ice. After 1 hour the precipitate was collected, digested with water (2.5 l), filtered off and dried, yielding 180-270 g of a product containing 69-81% of the desired barbituric acid (by titration of the CH2), the remaining 19-31% consisting mainly of 1-cyclohexyl-2-acetyl-3-(2-sulphamoylphenyl)barbituric acid, as determined by TLC and NMR.

Aufarbeitung

  1. temperaturewas refluxed for 4 hours
  2. stirringstirred for 1 hour

Quellen und Nachweise

ORD-Eintrag
ord-2c633d62dea0471fada9fa805b2a597f
Quelldatensatz
uspto-grants-1977_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04042397

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