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Sodium Methoxide → HCID 68700919, 화합물

HRID 1799488
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HRID 1799488 반응식
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11](Br)=[N:10][N:9]([C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[C:8]2=[O:23])=[CH:4][CH:3]=1.[CH3:26][O-:27].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([O:27][CH3:26])=[N:10][N:9]([C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[C:8]2=[O:23])=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 68704513HCID 68704513, 화합물

생성물 1

HCID 68700919HCID 68700919, 화합물수율 57%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

According to Scheme 2 Step 4: To a stirred solution of 3-(4-(4-chlorobenzyl)-6-bromo-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)benzonitrile (0.300 g, 0.72 mmol) in DMF (5 ml) was added, dropwise, at 0° C., 2M solution of sodium methoxide (0.72 mmol, 0.359 ml). The mixture was stirred 1 hour at 0° C. then quenched with water and extracted with ethyl acetate (×3). The combined organic layers were successively washed with water then with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography, 10 g prepacked column, DCM 100%. 150 mg (Yield=57%) of 3-(4-(4-chlorobenzyl)-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)benzonitrile were recovered and used for the next step.

후처리

  1. customat 0° C.
  2. customthen quenched with water
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic layers were successively washed with water
  5. dry with materialwith brine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography, 10 g

출처 및 근거

ORD 기록
ord-02803722236e444ab4ef6fd3585c8d80
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08344138B2

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