Ethyl iodoacetate → Ethyl 4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylate

HRID 1926600ノート

反応式

HRID 1926600 の反応式
[N:1]1([C:7](=[S:11])[CH2:8][C:9]#[N:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=O.CCN(C(C)C)C(C)C.I[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>C(#N)C>[C:9]([C:8]1[C:15]([C:14]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:13]=2[Cl:12])=[C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[S:11][C:7]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)#[N:10]

参加物

6

反応物 4

HCID 12183Ethyl iodoacetateHCID 666452,4-Dichlorobenzoyl chlorideHCID 81531Diisopropylethylamine2 回HCID 451589413-Morpholin-4-yl-3-thioxopropanenitrile

生成物 1

HCID 44155898Ethyl 4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylate収率 28%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 3-morpholin-4-yl-3-thioxopropanenitrile (0.150 g, 0.88 mmol) in anhydrous ACN (1.2 mL) was cooled to 0° C. To this cooled solution was added of 2,4-dichlorobenzoyl chloride (0.149 mL, 1.06 mmol) and DIPEA (0.161 mL, 0.93 mmol). The mixture was allowed to stir at rt under nitrogen for 15 min before ethyl iodoacetate (0.110 mL, 0.93 mmol) and DIPEA (0.161 mL, 0.93 mmol) were added. The reaction mixture was subjected to MWI at 140° C. for 10 min. The mixture was allowed to cool and was concentrated. The residue was purified by column chromatography to give ethyl 4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylate (0.1 g, 28%). LCMS: (AA) ES+ 411. 1H NMR (400 MHz, d1-chloroform) δ: 7.49 (d, 1H), 7.33 (dd, 1H), 7.20 (d, 1H), 4.16-4.08 (m, 2H), 3.89-3.85 (m, 4H), 3.66-3.63 (m, 4H) and 1.12 (t, 3H).

後処理

  1. additionwere added
  2. temperatureto cool
  3. concentrationwas concentrated
  4. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-8c6c4d80600e4a06be60e61dd335f73a
出典データセット
uspto-grants-2012_05
特許番号
US08183240B2

反応ノート

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