Phenylacetyl chloride → N-Hexyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-2-phenylacetamide

HRID 261795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 261795
[CH3:1][C:2]1[S:6][C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:4][N:3]=1.C(N(CC)CC)C.[C:21]1([CH2:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[CH2:8]([N:7]([C:5]1[S:6][C:2]([CH3:1])=[N:3][N:4]=1)[C:28](=[O:29])[CH2:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Komponenten

5

Edukt 3

HCID 7679Phenylacetyl chloride2×HCID 8471Triethylamine2×HCID 21315314N-Hexyl-5-methyl-1,3,4-thiadiazol-2-amine

Produkt 1

HCID 21679768N-Hexyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)-2-phenylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

N-(5-Methyl-1,3,4-thiadiazol-2-yl)-hexylamine (5.98 g, 0.03 mole) in toluene (60 ml) was stirred together with triethylamine (4.59 ml) and phenylacetyl chloride (4.64 g, 0.03 mole) and refluxed overnight. Further triethylamine (4.6 ml) and phenylacetyl chloride (4 ml) were added and refluxing was continued for a further 24 hours. The mixture was evaporated to dryness, treated with water and extracted with chloroform. The chloroform extract was washed with 2N sodium hydroxide solution and with water, and was dried (Na2SO4), filtered and evaporated to yield the title product as an oil, b.p. 190° C./0.1 mm (8.03 g). This was recrystallised from ethanol to give the title compound as a solid, m.p. 90° C.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. temperaturerefluxing
  3. customThe mixture was evaporated to dryness
  4. additiontreated with water
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. washwas washed with 2N sodium hydroxide solution and with water
  8. dry with materialwas dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-07d9c8aab9f147bb90a196f863636bce
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04152442

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