Iodocyclohexane → N-[(6-{[(cyclohexyloxy)imino]methyl}pyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1258587

反応式

HRID 1258587 の反応式
[OH:1][N:2]=[CH:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][N:12]=[C:13]([C:20]2[N:24]([CH3:25])[N:23]=[N:22][N:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][CH:5]=1.[H-].[Na+].I[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CN(C=O)C.[Cl-].[Na+].O>[CH:29]1([O:1][N:2]=[CH:3][C:4]2[N:9]=[C:8]([CH2:10][O:11][N:12]=[C:13]([C:20]3[N:24]([CH3:25])[N:23]=[N:22][N:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

参加物

6

反応物 3

HCID 12289IodocyclohexaneHCID 24758Sodium hydrideHCID 136352703N-({6-[(hydroxyimino)methyl]pyridin-2-yl}methoxy)-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

生成物 1

HCID 86653140N-[(6-{[(cyclohexyloxy)imino]methyl}pyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine収率 43%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
45 °C

実験手順

To a stirred solution of N-({6-[(hydroxyimino)methyl]pyridin-2-yl}methoxy)-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.2 g, 0.593 mmol, 1 eq.) in 2.5 ml of dry DMF, was added NaH (0.024 g, 0.623 mmol, 1.05 eq.) in one portion. After 10 mins, 1-iodocyclohexane (0.130 g, 0.623 mmol, 1.05 eq.) was added rapid dropwise. Stirring was continued for 20 hrs and warmed at 45° C. for 4 hrs. “brine” was added and the reaction was extracted with EtOAc (2×75 ml). The combined organic layers were washed with water (2×), dried over MgSO4 and evaporated. The residue was purified by chromatography on silica gel to give N-[(6-{[(cyclohexyloxy)imino]methyl}pyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.107 g, 41% yield) as a colourless viscous oil.

後処理

  1. waitwas continued for 20 hrs
  2. extractionthe reaction was extracted with EtOAc (2×75 ml)
  3. washThe combined organic layers were washed with water (2×)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-681d2c49895346a9bfed02e951b9cc52
出典データセット
uspto-grants-2013_06
特許番号
US08466176B2

関連ノート

読み込み中…