Ammonia → N-(2-(4-methoxy-3-methylphenyl)ethyl)-1-(2-thienyl)cyclopropanecarboxamide

HRID 2393459

Reaktionsgleichung

Reaktionsgleichung von HRID 2393459
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][C:4]=1[CH3:12].C1(N=C=NC2CCCCC2)CCCCC1.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33]1([C:36](O)=[O:37])[CH2:35][CH2:34]1.ON1C2C=CC=CC=2N=N1.N>O1CCCC1.O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:36]([C:33]2([C:29]3[S:28][CH:32]=[CH:31][CH:30]=3)[CH2:35][CH2:34]2)=[O:37])=[CH:5][C:4]=1[CH3:12]

Komponenten

9

Edukt 5

HCID 222AmmoniaHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 64846602-(4-Methoxy-3-methylphenyl)ethan-1-amineHCID 189757061-(Thiophen-2-yl)cyclopropane-1-carboxylic acid

Produkt 1

HCID 18975656N-(2-(4-methoxy-3-methylphenyl)ethyl)-1-(2-thienyl)cyclopropanecarboxamideAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-methoxy-3-methylphenyl)ethylamine (16 g), triethylamine (1.74 ml), 1,3-dicyclohexylcarbodiimide (8.75 g), 1-(2-thienyl)cyclopropanecarboxylic acid (7 g) and 1-hydroxybenzotriazole (5.6 g) in tetrahydrofuran (95 ml) was stirred for 16 hours. The mixture was poured into water, basified with aqueous ammonia solution and filtered. The filtrate was extracted with ethyl acetate (3×50 ml) and the combined extracts washed with 1M hydrochloric acid and brine then dried and the solvent removed in vacuo. The resulting gum was treated with acetonitrile and insoluble matter filtered off. Evaporation of the filtrate gave crude N-[2-(4-methoxy-3-methylphenyl)ethyl]-1-(2-thienyl)cyclopropanecarboxamide as a solid (10.7 g), which was used without further purification.

Aufarbeitung

  1. filtrationfiltered
  2. extractionThe filtrate was extracted with ethyl acetate (3×50 ml)
  3. washthe combined extracts washed with 1M hydrochloric acid and brine
  4. customthen dried
  5. customthe solvent removed in vacuo
  6. additionThe resulting gum was treated with acetonitrile and insoluble matter
  7. filtrationfiltered off
  8. customEvaporation of the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-2647db0c64564123b3bfc870460661dd
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807868

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