Morpholine → 4-Amino-beta-(4-chlorophenyl)-3,5-dichloro-cinnamic acid morpholide

HRID 580603

Reaktionsgleichung

Reaktionsgleichung von HRID 580603
[NH2:1][C:2]1[C:19]([Cl:20])=[CH:18][C:5]([C:6]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:7][C:8]([OH:10])=O)=[CH:4][C:3]=1[Cl:21].C(N(CC)CC)C.ClC(OCC)=O.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:3]([Cl:21])=[CH:4][C:5]([C:6]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:7][C:8]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[O:10])=[CH:18][C:19]=1[Cl:20]

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 539436954-Amino-beta-(4-chlorophenyl)-3,5-dichloro-cinnamic acid

Produkt 1

HCID 545219194-Amino-beta-(4-chlorophenyl)-3,5-dichloro-cinnamic acid morpholide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

20 g (0.058 mol) of 4-amino-β-(4-chlorophenyl)-3,5-dichloro-cinnamic acid (mixture of isomers A and B in the ratio 1:1.5) were dissolved in 700 ml of dry chloroform. 5.93 g (0.058 mol) of triethylamine were added while cooling with ice and stirring, and the mixture was cooled to -10° C. and combined with 6.35 g (0.058 mol) of ethyl chloroformate. After the addition had ended, 25.5 g (0.29 mol) of morpholine were added while further stirring and cooling. The resulting mixture was stirred for 4 hours more at room temperature and then extracted three times with water, and the organic phase was dried over sodium sulfate and concentrated to dryness in vacuo. The residue was chromatographed on a silica gel column (silica gel: substance=10:1, eluant: chloroform/ethyl acetate=1:1). The eluates containing substance were combined and evaporated to dryness in vacuo. Colorless crystals were obtained, melting point 140°-144° C., which contained the cis/trans isomer mixture in a proportion of 3:2.

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. additionAfter the addition
  3. stirringwhile further stirring
  4. temperaturecooling
  5. stirringThe resulting mixture was stirred for 4 hours more at room temperature
  6. extractionextracted three times with water
  7. dry with materialthe organic phase was dried over sodium sulfate
  8. concentrationconcentrated to dryness in vacuo
  9. customThe residue was chromatographed on a silica gel column (silica gel: substance=10:1, eluant: chloroform/ethyl acetate=1:1)
  10. additionThe eluates containing substance
  11. customevaporated to dryness in vacuo
  12. customColorless crystals were obtained

Quellen und Nachweise

ORD-Eintrag
ord-4b56859e3dd44daca0e2020c3203dfc8
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04753934

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