Sodium Carbonate → HCID 21319731, Verbindung

HRID 2071348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2071348
C[O-].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:17])[N:14](C)C)[CH:8]=[CH:9][C:10]=1[OH:11].[Na].[CH3:19][C:20]([O:24][CH2:25]Cl)([CH3:23])[C:21]#[CH:22].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O>[Cl:4][C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:17])[NH2:14])[CH:8]=[CH:9][C:10]=1[O:11][CH2:25][O:24][C:20]([CH3:23])([CH3:19])[C:21]#[CH:22]

Komponenten

8

Edukt 5

HCID 10340Sodium CarbonateHCID 182205N'-(3-Chloro-4-hydroxyphenyl)-N,N-dimethylcarbamimidic acidHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 13694639HCID 13694639, Verbindung

Produkt 1

HCID 21319731HCID 21319731, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium methoxide (0.54 gram, 0.01 mole) is added to a methanolic solution of 3-(3-chloro-4-hydroxyphenyl)-1,1-dimethylurea (2.14 grams, 0.01 mole) and the mixture heated at reflux during 2 hours. The solvent is removed under reduced pressure and to the residual material dry benzene is added and evaporated off. This procedure is repeated until a dry white powder is obtained. The sodium salt is suspended in dry acetone (50 ml.) and chloromethyl 1,1-dimethyl-2-propynyl ether (1.45 grams, 0.011 mole) is added dropwise with stirring. After the initial exothermic reaction the reaction mixture is allowed to stir for a further 4.5 hours, then cold aqueous sodium carbonate solution (10% w/v, 100 ml.) followed by water (50 ml.) are added(1) and stirred. The resulting solid(2) is filtered off, water washed and air dried. Crystallization from benzene-hexane affords 2.2 grams, 70%; melting point 150° C. to 151° C. of Compound 1.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux during 2 hours
  3. customThe solvent is removed under reduced pressure and to the residual material dry benzene
  4. additionis added
  5. customevaporated off
  6. customis obtained
  7. customAfter the initial exothermic reaction the reaction mixture
  8. stirringto stir for a further 4.5 hours
  9. stirringstirred
  10. filtrationThe resulting solid(2) is filtered off
  11. washwater washed
  12. customair dried
  13. customCrystallization from benzene-hexane
  14. customaffords 2.2 grams, 70%

Quellen und Nachweise

ORD-Eintrag
ord-5d7ca8aed7cc46d6a9e037902a9cdc29
Quelldatensatz
uspto-grants-1977_09
Patentnummer
US04046808

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