Acetic Anhydride → 2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

HRID 1885370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885370
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17](O)=O)[N:9]([C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH3:10])=[CH:4][CH:3]=1.ClC(=C)[C:22]#[N:23].[C:25](OC(=O)C)(=O)C.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:10])[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:25][C:17]=2[C:22]#[N:23])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 109901014-Chloro-α-[methyl(2,2,2-trifluoroacetyl)amino]benzeneacetic acid

Produkt 1

HCID 118221892-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 2-(p-chlorophenyl)-N-(trifluoroacetyl)sarcosine (147.7 g, 0.50 mol) in acetonitrile is treated dropwise with α-chloroacrylonitrile (54.7 g, 0.62 mol) and acetic anhydride (153 g, 1.5 mol), stirred vigorously, treated dropwise with triethylamine (58.1 g, 0.57 mol) at 56°-60° C. over a 11/4 hour period, heated at 60° C. for 16 hours and concentrated in vacuo to give a residue. The residue is partitioned between ethyl acetate and water. The organic phase is concentrated in vacuo to afford an amber solid residue. Said solid is purified by flash chromatography (silica; ethyl acetate/hexanes) and recrystallized from methanol to give the title product as a pale yellow solid, mp 129.5°-130.5° C.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customto give a residue
  3. customThe residue is partitioned between ethyl acetate and water
  4. concentrationThe organic phase is concentrated in vacuo
  5. customto afford an amber solid residue
  6. customis purified by flash chromatography (silica; ethyl acetate/hexanes)
  7. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-97ed2fd1de4546a3b2b70d1f4686699d
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05144041

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