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

HRID 2039685ノート

反応式

HRID 2039685 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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].

後処理

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

出典と根拠

ORDレコード
ord-ed7bd2a38cd44a0ea4d6f27926ed801c
出典データセット
uspto-grants-2013_11
特許番号
US08580799B2

反応ノート

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