Isoamyl Nitrite → 4-Cyano-3-iodo-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

HRID 1990072ノート

反応式

HRID 1990072 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:14]([F:17])([F:16])[F:15])=[C:9]([C:12]#[N:13])[C:10]=1N)=[O:5])[CH3:2].[I:18]C1CC(C(C)C)CCC1(I)C.N(OCCC(C)C)=O>CC#N>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:14]([F:17])([F:16])[F:15])=[C:9]([C:12]#[N:13])[C:10]=1[I:18])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 8053Isoamyl NitriteHCID 685236583-Amino-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl esterHCID 86612408Diiodomenthane

生成物 1

HCID 685208084-Cyano-3-iodo-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

Combine 3-amino-4-cyano-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester, prepared in preparation 45, (1.12 mmol), diiodomenthane (3.92 mmol), and isoamyl nitrite (2.8 mmol) in CH3CN and heat to 80° C. After 45 minutes, cool to room temperature and concentrate in vacuo. Purify the dark residue by flash chromatography eluting with methylene chloride. Concentration of desired fractions and recrystallization from hexanes provides the title compound: 1H NMR (400 MHz, CDCl3) δ 4.45 (q, 2H, J=7.2 Hz) and 1.44 (t, 3H, J=7.3 Hz), 19F NMR (CDCl3) δ—57.6 ppm (s).

後処理

  1. temperaturecool to room temperature
  2. concentrationconcentrate in vacuo
  3. customPurify the dark residue by flash chromatography
  4. washeluting with methylene chloride
  5. customConcentration of desired fractions and recrystallization from hexanes

出典と根拠

ORDレコード
ord-4b3d1d8f2561494594ef4e0ec7eaab49
出典データセット
uspto-grants-2010_01
特許番号
US07642361B2

反応ノート

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