Sodium Hydroxide → Rabeprazole-thioether

HRID 226227ノート

反応式

HRID 226227 の反応式
Cl[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1.[N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[NH:18][C:17]=1[SH:25].[OH-].[Na+]>C(O)C>[CH3:15][O:14][CH2:13][CH2:12][CH2:11][O:10][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][S:25][C:17]2[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:16]=2)[C:8]=1[CH3:9]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 110316672-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridineHCID 178527775HCID 178527775、化合物

生成物 1

HCID 9949996Rabeprazole-thioether収率 101%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-Chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine (53.2 g (200 mmol)), denatured ethanol (320 ml), 2-benzimidazolethiol (30.2 g (201 mmol)), and sodium hydroxide (26.8 g (670 mmol)) were added together, and reaction was carried out for approximately 2 hours at 50° C. After it had been confirmed by TLC that the starting material had disappeared, vacuum concentration was carried out, and ethyl acetate (430 ml) and water (340 ml) were then added. After stirring and then leaving to stand, the aqueous layer was separated off. The organic layer was washed with a 10% sodium hydroxide aqueous solution (110 ml), and twice with water (110 ml), and then vacuum concentration was carried out, thus obtaining crude 2-[{4-(3-methoxypropoxy)-3-methylpyridin-2-yl}methylthio]-1H-benzimidazole (69.0 g) (HPLC purity 98.7%, yield 101%).

後処理

  1. customreaction
  2. concentrationvacuum concentration
  3. additionethyl acetate (430 ml) and water (340 ml) were then added
  4. customleaving
  5. customthe aqueous layer was separated off
  6. washThe organic layer was washed with a 10% sodium hydroxide aqueous solution (110 ml)
  7. concentrationtwice with water (110 ml), and then vacuum concentration

出典と根拠

ORDレコード
ord-8cdaa3119709404ca10b23f3c7266449
出典データセット
uspto-grants-2009_07
特許番号
US07557217B2

反応ノート

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