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

HRID 1926600노트

반응식

HRID 1926600 반응식
[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]

참가 물질

6

반응물 4

HCID 12183Ethyl iodoacetateHCID 666452,4-Dichlorobenzoyl chlorideHCID 81531Diisopropylethylamine2회HCID 451589413-Morpholin-4-yl-3-thioxopropanenitrile

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8c6c4d80600e4a06be60e61dd335f73a
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183240B2

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