Potassium Iodide → 2-[6-[[(Z)-[(4-methyl-1,2,5-thiadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]-2-pyridinyl]isoindole-1,3-dione

HRID 2039685노트

반응식

HRID 2039685 반응식
[OH:1][N:2]=[C:3]([C:10]1[C:14]([CH3:15])=[N:13][S:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:17][C:18]1[N:23]=[C:22]([N:24]2[C:32](=[O:33])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]2=[O:34])[CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O>[CH3:15][C:14]1[C:10](/[C:3](=[N:2]\[O:1][CH2:17][C:18]2[N:23]=[C:22]([N:24]3[C:25](=[O:34])[C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:32]3=[O:33])[CH:21]=[CH:20][CH:19]=2)/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[N:11][S:12][N:13]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dioneHCID 136351090N-hydroxy-1-(4-methyl-1,2,5-thiadiazol-3-yl)-1-phenylmethanimine

생성물 1

HCID 873948112-[6-[[(Z)-[(4-methyl-1,2,5-thiadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]-2-pyridinyl]isoindole-1,3-dione수율 82%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of N-hydroxy-1-(4-methyl-1,2,5-thiadiazol-3-yl)-1-phenylmethanimine (24.3 g, 111 mmol) in dry acetonitrile (600 mL) were added 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (36.9 g, 116 mmol), cesium carbonate (37.9 g, 116 mmol) and potassium iodide (1.84 g, 11 mmol). The reaction mixture was stirred at room temperature for 14 h, then diluted with water (200 mL) and concentrated in vacuo. The residue was extracted with ethyl acetate (2×300 mL). The combined organic layers were combined and concentrated in vacuo to afford 2-{6-[({[(Z)-(4-methyl-1,2,5-thiadiazol-3-yl)(phenyl)methylene]amino}-oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione as a red oil [49 g, yield 82%; HPLC/MS: m/z=456 (M+H); log P(HCOOH)=3.99].

후처리

  1. concentrationconcentrated in vacuo
  2. extractionThe residue was extracted with ethyl acetate (2×300 mL)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ed7bd2a38cd44a0ea4d6f27926ed801c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580799B2

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