Sulfuric Acid → N-[1,1-dimethyl(3-pyridyl)butyl]-2-nitrobenzeneacetamide

HRID 1651098

Reaktionsgleichung

Reaktionsgleichung von HRID 1651098
[CH3:1][CH:2]([CH3:12])[CH2:3][CH:4]=[CH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]#[N:24])([O-:15])=[O:14].S(=O)(=O)(O)[OH:26]>C(O)(=O)C>[CH3:1][C:2]([NH:24][C:23](=[O:26])[CH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N+:13]([O-:15])=[O:14])([CH3:12])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 118882-NitrophenylacetonitrileHCID 54005742HCID 54005742, Verbindung

Produkt 1

HCID 14347488N-[1,1-dimethyl(3-pyridyl)butyl]-2-nitrobenzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 22.7 g of 3-(4-methyl-pentenyl)pyridine and 22.8 g of 2-nitrobenzeneacetonitrile in 80 mL of acetic acid was cooled to 12°-13° C. and then 16 mL of sulfuric acid was added dropwise over 6 minutes. The reaction was stirred for 2 hours at ambient temperature, then after the acetic acid was removed in vacuo, 1L of water was added and the mixture was extracted with dichloromethane to remove neutral impurities. The aqueous layer was basified with 10N sodium hydroxide, and extracted with dichloromethane (4×200 mL). The dried (K2CO3) extracts were evaporated to give 35.6 g of N-[1.1-dimethyl(3-pyridyl)butyl]-2-nitrobenzeneacetamide. A portion was crystallized from ethyl acetate-hexane to yield the analytical sample, mp 117°-118.5° C.

Aufarbeitung

  1. temperaturewas cooled to 12°-13° C.
  2. customafter the acetic acid was removed in vacuo, 1L of water
  3. additionwas added
  4. extractionthe mixture was extracted with dichloromethane
  5. customto remove neutral impurities
  6. extractionextracted with dichloromethane (4×200 mL)
  7. dry with materialThe dried (K2CO3) extracts
  8. customwere evaporated

Quellen und Nachweise

ORD-Eintrag
ord-782f57be288448e282abed053a7e139f
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927826

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