Acrylonitrile → Tralopyril

HRID 1358787

反応式

HRID 1358787 の反応式
Cl[CH:2]([N:7]=[C:8](Cl)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:3]([F:6])([F:5])[F:4].[C:17](#[N:20])[CH:18]=[CH2:19].C(N(CC)C(C)C)(C)C.[Br:30]Br>CN(C)C=O.CCCCCCC.C(OCC)(=O)C>[Br:30][C:19]1[C:18]([C:17]#[N:20])=[C:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[NH:7][C:2]=1[C:3]([F:6])([F:5])[F:4]

参加物

8

反応物 4

HCID 7855AcrylonitrileHCID 24408BromineHCID 81531DiisopropylethylamineHCID 72751476N-[1-chloro-(2,2,2-trifluoroethyl)]-4-chlorobenzimidoyl chloride

生成物 1

HCID 183559Tralopyril収率 22.9%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 8900Heptane溶媒

実験手順

A solution of N-[1-chloro-(2,2,2-trifluoroethyl)]-4-chlorobenzimidoyl chloride (5.80 g, 0.02 mol) and acrylonitrile (1.33 g, 0.025 mol) in N,N-dimethylformamide (15 mL) under a nitrogen atmosphere is treated with N,N-diisopropylethylamine (DIPEA, 7.8 g, 0.06 mol) over 30 minutes, heated to and held at 45-47° C. for 18 hours, cooled to room temperature, treated with bromine (3.2 g, 0.02 mol), stirred at room temperature for 1 hour, quenched with water, and extracted with ethyl acetate. The organic extract is concentrated in vacuo to obtain a residue. Flash column chromatography of the residue on silica gel, packed with 15% ethyl acetate in heptane and eluted with 20% ethyl acetate in heptane, gives the title product as white solid (1.6 g, 22.9% yield) which is identified by 1H and 19F NMR spectral analyses.

後処理

  1. temperatureheated to and
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. concentrationis concentrated in vacuo
  6. customto obtain a residue
  7. washeluted with 20% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-cd3be75980be4c36b45f7bc664701e92
出典データセット
uspto-grants-2003_07
特許番号
US06596902B2

関連ノート

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