Water → HCID 70574177, Verbindung

HRID 1388982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1388982
O.Br[CH2:3][C:4](=O)[CH:5](C)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:7].[C:18]([NH:23][C:24]([NH2:26])=[S:25])(=[O:22])[CH:19]([CH3:21])[CH3:20].N1C=CC=C[CH:28]=1>C(O)C>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:6]([CH2:5][CH:4]=[C:3]2[CH2:28][S:25][C:24]([NH:23][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])=[N:26]2)=[O:7])=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 3555130N-Carbamothioyl-2-methylpropanamideHCID 20297521HCID 20297521, Verbindung

Produkt 1

HCID 70574177HCID 70574177, VerbindungAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A 300 ml reaction flask fitted with a magnetic stirrer, heating mantle, thermometer and water-cooled condenser was charged with 5.0 g (0.016 mole) of 4-bromo-4'-chloro-2-methylacetoacetanilide [M.P. 103°-105°; prepared as described by Hodgkinson and Staskun in The Journal of Organic Chemistry, vol. 34, p. 1710 (1969)], 100 ml of ethanol, 2.5 g (0.017 mole) of N-isobutyrylthiourea [M.P. 112°-114°; prepared as described by Moore and Crossley in The Journal of the American Chemical Society, vol. 62, p. 3273 (1940)] and 1.6 g (0.02 mole) of pyridine. The solution was stirred and refluxed for three hours. The solvent was removed under reduced pressure and the residual solid was stirred with watertoluene. There was obtained 3.9 g (69%) of white solid, M.P. 202°-204°. N.M.R. (dimethyl-d6 sulfoxide)∂1.1-1.3 (2×CH3), 1.4-1.6 (CH3, doublet), 3.5-4.0 (2×CH), 6.8 (hetero-aromatic), 7.2-7.7 (aromatic).

Aufarbeitung

  1. customA 300 ml reaction flask
  2. customfitted with a magnetic stirrer
  3. temperatureheating mantle
  4. customprepared
  5. customprepared
  6. temperaturerefluxed for three hours
  7. customThe solvent was removed under reduced pressure
  8. stirringthe residual solid was stirred with watertoluene

Quellen und Nachweise

ORD-Eintrag
ord-4599fd214cee49afa537849fceb12f29
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04243407

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