p-Toluenesulfonic acid → 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridine-2-carbaldehyde

HRID 1258584ノート

反応式

HRID 1258584 の反応式
[O:1]1CCO[CH:2]1[C:6]1[N:11]=[C:10]([CH2:12][O:13][N:14]=[C:15]([C:22]2[N:26]([CH3:27])[N:25]=[N:24][N:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=[CH:8][CH:7]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CS(C)=O.O.CCOC(C)=O>[CH3:27][N:26]1[C:22]([C:15](=[N:14][O:13][CH2:12][C:10]2[N:11]=[C:6]([CH:2]=[O:1])[CH:7]=[CH:8][CH:9]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:23][N:24]=[N:25]1

参加物

6

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 86653136N-{[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

生成物 1

HCID 866531376-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridine-2-carbaldehyde収率 106.9%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a solution of N-{[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (3.3 g, 9 mmol, 1 eq.) in 75 ml of DMSO and 15 ml of water was added p-TSA (1.79 g, 9.45 mmol, 1.05 eq.). The reaction was heated to 100° C. for 1.5 hrs. After cooling to room temperature, the mixture was diluted with 400 ml of EtOAc, washed with sat. aqueous NaHCO3, followed by water (×2). The organic layer was separated, dried over MgSO4 and concentrated to give 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridine-2-carbaldehyde (3.1 g, 96% yield) as a viscous yellow oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with sat. aqueous NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-31e536262a7041e281c21674b3d64591
出典データセット
uspto-grants-2013_06
特許番号
US08466176B2

反応ノート

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