3-Chloro-4-(propan-2-yloxy)aniline → 4'-(Isopropoxy)-3'-chloro-1-methoxycyclopropanecarboxanilide

HRID 1862799

Reaktionsgleichung

Reaktionsgleichung von HRID 1862799
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])[NH2:5].[CH3:13][O:14][C:15]1([C:18](OC)=[O:19])[CH2:17][CH2:16]1.C[O-].[Na+]>C1C=CC=CC=1>[CH:10]([O:9][C:8]1[CH:7]=[CH:6][C:4]([NH:5][C:18]([C:15]2([O:14][CH3:13])[CH2:17][CH2:16]2)=[O:19])=[CH:3][C:2]=1[Cl:1])([CH3:12])[CH3:11]

Komponenten

5

Edukt 3

HCID 65003943-Chloro-4-(propan-2-yloxy)anilineHCID 10942334Sodium MethoxideHCID 20393514Methyl 1-methoxycyclopropanecarboxylate

Produkt 1

HCID 203934954'-(Isopropoxy)-3'-chloro-1-methoxycyclopropanecarboxanilideAusbeute 21,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture consisting of 5.6 g of 3-chloro-4-isopropoxyaniline, 3.9 g of methyl 1-methoxycyclopropanecarboxylate and 1.8 g of sodium methoxide in 50 ml of benzene was refluxed for 3 hours. The reaction mixture was concentrated to a volume of 25 ml, poured over ice water, acidified with hydrochloric acid and extracted with ether. The extract was dried, filtered and concentrated. Purification by silica chromatography gave 1.8 g of product as a white crystalline solid; m.p. 86°-87° C.

Aufarbeitung

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated to a volume of 25 ml
  3. additionpoured over ice water
  4. extractionextracted with ether
  5. customThe extract was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c074bb11e621450291b7f0814b895cf7
Quelldatensatz
uspto-grants-1979_09
Patentnummer
US04166735

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