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

HRID 1885370노트

반응식

HRID 1885370 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-97ed2fd1de4546a3b2b70d1f4686699d
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05144041

반응 노트

불러오는 중…