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

HRID 1651199

Reaktionsgleichung

Reaktionsgleichung von HRID 1651199
[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, 1 L 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, 1 L 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-84b78144629743388c7fde5ff36d5a83
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927838

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