Reaktion #349201

Reaktionsgleichung

sodium carbonate

sodium

chloromethyl 1,1-dimethyl-2-propynyl ether

Sodium methoxide

3-(3-chloro-4-hydroxyphenyl)-1,1-dimethylurea

→

3-[3-Chloro-4-[(1,1-dimethyl-2-propynyloxy)methoxy]phenyl]urea

Lösungsmittel

acetone

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturat reflux during 2 hours
3. 3
   SonstigeThe solvent is removed under reduced pressure and to the residual material dry benzene
4. 4
   workup.ADDITIONis added
5. 5
   Sonstigeevaporated off
6. 6
   Sonstigeis obtained
7. 7
   SonstigeAfter the initial exothermic reaction the reaction mixture
8. 8
   workup.STIRRINGto stir for a further 4.5 hours
9. 9
   workup.STIRRINGstirred
10. 10
    FiltrationThe resulting solid(2) is filtered off
11. 11
    Waschenwater washed
12. 12
    Sonstigeair dried
13. 13
    SonstigeCrystallization from benzene-hexane
14. 14
    Sonstigeaffords 2.2 grams, 70%

Vorschrift

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.

Quelle