Triethylamine → alpha-(1-Methyl-3-methoxymethylpyrazol-4-ylcarbonylamino)-(2-furyl)acetonitrile

HRID 414606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414606
Cl.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]([NH2:10])[C:8]#[N:9].C(N(CC)CC)C.[CH3:18][N:19]1[CH:23]=[C:22]([C:24](Cl)=[O:25])[C:21]([CH2:27][O:28][CH3:29])=[N:20]1.Cl.C(N(CC)CC)C>C(OCC)(=O)C.O>[CH3:18][N:19]1[CH:23]=[C:22]([C:24]([NH:10][CH:7]([C:3]2[O:2][CH:6]=[CH:5][CH:4]=2)[C:8]#[N:9])=[O:25])[C:21]([CH2:27][O:28][CH3:29])=[N:20]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 13075762HCID 13075762, VerbindungHCID 143294173-(Methoxymethyl)-1-methylpyrazole-4-carbonyl chloride

Produkt 1

HCID 14329418alpha-(1-Methyl-3-methoxymethylpyrazol-4-ylcarbonylamino)-(2-furyl)acetonitrileAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 100 ml of ethyl acetate was suspended 3.2 g of alpha-(2-furyl)-aminoacetonitrile hydrochloride, and with ice cooling, 4.5 g of triethylamine was added. Then, 3.8 g of 1-methyl-3-methoxymethylpyrazole-4-carboxylic acid chloride was gradually added at 0° to 5° C. with stirring. After the addition, the mixture was further stirred at room temperature for 2 hours. Water (50 ml) was added to dissolve the precipitated triethylamine hydrochloride. The ethyl acetate layer was separated, washed with water, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was chromatographed on a silica gel column, and the column was eluted with hexane/ethyl acetate to give 4.3 g (yield 78.6%) of the desired alpha-(1-methyl-3-methoxymethylpyrazol-4-ylcarbonylamino)-(2-furyl)acetonitrile.

Aufarbeitung

  1. additionAfter the addition
  2. stirringthe mixture was further stirred at room temperature for 2 hours
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was chromatographed on a silica gel column
  9. washthe column was eluted with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ad8b308f479049099452cf0250976f47
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04792565

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