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

HRID 1990072노트

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HRID 1990072 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4b3d1d8f2561494594ef4e0ec7eaab49
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642361B2

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