Water → 2,6-dichloro-N-(2-chloroethyl)benzamide

HRID 846735

Reaktionsgleichung

Reaktionsgleichung von HRID 846735
Cl.[Cl:2][CH2:3][CH2:4][NH2:5].C(=O)([O-])[O-].[K+].[K+].O.[Cl:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:15]=1[C:16](Cl)=[O:17]>ClCCl>[Cl:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:15]=1[C:16]([NH:5][CH2:4][CH2:3][Cl:2])=[O:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 783922,6-Dichlorobenzoyl chlorideHCID 97937372-Chloroethylamine hydrochloride

Produkt 1

HCID 150969722,6-dichloro-N-(2-chloroethyl)benzamideAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred (vigourously) mixture of 17.4 parts of 2-chloroethanamine hydrochloride, 20.7 parts of potassium carbonate and 225 parts of water was added dropwise a mixture of 31.3 parts of 2,6-dichlorobenzoyl chloride and 120 parts of dichloromethane at room temperature: slightly exothermic reaction. Upon completion, stirring at room temperature was continued for one hour. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with water, dried, filtered and evaporated. The residue was crystallized from methylbenzene. The product was filtered off and dried, yielding 25.8 parts (68.8%) of 2,6-dichloro-N-(2-chloroethyl)benzamide; mp. 113.8° C. (intermediate 30).

Aufarbeitung

  1. additionwas added dropwise
  2. customslightly exothermic reaction
  3. stirringUpon completion, stirring at room temperature
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with dichloromethane
  6. washThe combined organic phases were washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was crystallized from methylbenzene
  11. filtrationThe product was filtered off
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-bf3978f797af4bb1ad7ab7e46300bdba
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137896

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