Water → Ethyl 2-((diphenylmethylene)amino)-2-(pyrazin-2-yl)acetate

HRID 336339

反応式

HRID 336339 の反応式
[C:1]1([C:7](=[N:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:22]1[CH:27]=[N:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN1CCCC1=O>[C:1]1([C:7](=[N:14][CH:15]([C:22]2[CH:27]=[N:26][CH:25]=[CH:24][N:23]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 6428002-Bromopyrazine

生成物 1

HCID 10246971Ethyl 2-((diphenylmethylene)amino)-2-(pyrazin-2-yl)acetate

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
110 °C

実験手順

A mixture of ethyl 2-((diphenylmethylene)amino)acetate (6.0 g, 22.47 mmol), 2-bromopyrazine (7.1 g, 44.90 mmol), potassium carbonate (9.30 g, 67.40 mmol) and tetrabutyl ammonium iodide (8.10 g, 22.40 mmol) in N-methyl-2-pyrrolidone (25 mL) was heated in a sealed tube at 110° C. for 16 hours. The mixture was poured into water (100 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were washed with brine (25 mL) and dried over sodium sulfate. Removal of solvent under vacuum afforded crude product which was purified in Combi-Flash instrument using a gradient of methanol in chloroform. Yield: 4.90 g (63%). 1H NMR (300 MHz, DMSO-d6) δ: 1.16 (t, 3H), 4.07 (q, 2H), 5.26 (s, 1H), 7.18 (dd, 2H), 7.38-7.61 (m, 8H), 8.56 (d, 1H), 8.57 (d, 1H), 8.60 (s, 1H). MS (ES) MH+: 346.3 for C21H19N3O2.

後処理

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe organic layers were washed with brine (25 mL)
  3. dry with materialdried over sodium sulfate
  4. customRemoval of solvent under vacuum
  5. customafforded crude product which
  6. customwas purified in Combi-Flash instrument

出典と根拠

ORDレコード
ord-3c5640f5596048ceb5e6ad6d3633d084
出典データセット
uspto-grants-2014_11
特許番号
US08889671B2

関連ノート

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