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

HRID 716025

반응식

HRID 716025 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-094f83a8dfc0419ba98afa68f10fb329
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187495B2

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