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

HRID 1885370ノート

反応式

HRID 1885370 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-97ed2fd1de4546a3b2b70d1f4686699d
出典データセット
uspto-grants-1992_09
特許番号
US05144041

反応ノート

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