Toluene → Benzamide, 3-bromo-5-chloro-2,6-dimethoxy-N-(1-ethyl-2-pyrrolidinylmethyl)-

HRID 224425

Reaktionsgleichung

Reaktionsgleichung von HRID 224425
S(Cl)(Cl)=O.[Br:5][C:6]1[C:7]([O:18][CH3:19])=[C:8]([C:12]([O:16][CH3:17])=[C:13]([Cl:15])[CH:14]=1)[C:9]([OH:11])=O.C1(C)C=CC=CC=1.[NH2:27][CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][N:30]1[CH2:34][CH3:35]>C(C(C)=O)C.CCOCC>[CH2:34]([N:30]1[CH2:31][CH2:32][CH2:33][CH:29]1[CH2:28][NH:27][C:9](=[O:11])[C:8]1[C:12]([O:16][CH3:17])=[C:13]([Cl:15])[CH:14]=[C:6]([Br:5])[C:7]=1[O:18][CH3:19])[CH3:35]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 28004633-Bromo-5-chloro-2,6-dimethoxybenzoic acid

Produkt 1

HCID 54942Benzamide, 3-bromo-5-chloro-2,6-dimethoxy-N-(1-ethyl-2-pyrrolidinylmethyl)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

20 ml of thionyl chloride is added to 11.82 g (0.04 mol) of 3-bromo-5-chloro-2,6-dimethoxybenzoic acid. The mixture is heated on a steam bath for 1 hour. To the solution is added 50 ml of toluene. The solvent and excess thionyl chloride is evaporated at reduced pressure. The residue is dissolved in 50 ml of dry methyl ethyl ketone. The solution is added dropwise while stirring to 5.13 g (0.04 mol) 2-(aminomethyl)-1-ethylpyrrolidine in 50 ml methyl ethyl ketone. After stirring for 30 minutes at room temperature 300 ml of ether is added. The obtained semisolid product is separated and dissolved in 300 ml of water. Sodium hydroxide solution is added while stirring and cooling in ice. The precipitate is collected and washed with water. Yield: 12.0 g, m.p. 124°-25° C.

Aufarbeitung

  1. temperatureThe mixture is heated on a steam bath for 1 hour
  2. customThe solvent and excess thionyl chloride is evaporated at reduced pressure
  3. dissolutionThe residue is dissolved in 50 ml of dry methyl ethyl ketone
  4. additionThe solution is added dropwise
  5. additionis added
  6. customThe obtained semisolid product is separated
  7. dissolutiondissolved in 300 ml of water
  8. additionSodium hydroxide solution is added
  9. temperaturecooling in ice
  10. customThe precipitate is collected
  11. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-1fe9d75322c342f4be60438897c1fb7b
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04232037

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