Methanol → 1-(2-cyanoethyl)-1H-benzoimidazole-5-carboxylic acid

HRID 555285ノート

反応式

HRID 555285 の反応式
C[O:2][C:3]([C:5]1[CH:17]=[CH:16][C:8]2[N:9]([CH2:12][CH2:13][C:14]#[N:15])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-].CO>C1COCC1.O>[C:14]([CH2:13][CH2:12][N:9]1[C:8]2[CH:16]=[CH:17][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[N:11]=[CH:10]1)#[N:15]

参加物

6

反応物 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 669871661-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester

生成物 1

HCID 669873251-(2-cyanoethyl)-1H-benzoimidazole-5-carboxylic acid収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(2-cyanoethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (4.0 g, 17.4 mmol) in THF (30 mL) was added LiOH (1.67 g, 69.79 mmol) in water (8 mL) followed by MeOH (2 mL). Stirring continued at the ambient temperature for 1 h. It was then concentrated and acidified with 2N HCl. The solids formed were filtered and dried which afforded 1-(2-cyanoethyl)-1H-benzoimidazole-5-carboxylic acid (3.5 g, 95%). 1H NMR (300 MHz, DMSO-d6) δ 3.1 (t, 2H), 4.6 (t, 2H), 7.8 (d, 1H), 7.9 (dd, 1H), 8.25 (d, 1H), 8.42 (s, 1H)

後処理

  1. concentrationIt was then concentrated
  2. customThe solids formed
  3. filtrationwere filtered
  4. customdried which

出典と根拠

ORDレコード
ord-670233ff91fb4bdcb0453d61c2c8be73
出典データセット
uspto-grants-2011_11
特許番号
US08053431B2

反応ノート

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