Water → HCID 70546223、化合物

HRID 1759250ノート

反応式

HRID 1759250 の反応式
[OH:1][C:2]1[C:3]([CH2:8][C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[C:16]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)#[N:17].O>CN(C)C=O>[C:16]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:1][C:2]2[C:3]([CH2:8][C:9]3[NH:13][CH:12]=[CH:11][N:10]=3)=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:20][CH:19]=1)#[N:17]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 70545010HCID 70545010、化合物

生成物 1

HCID 70546223HCID 70546223、化合物収率 120.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 3-hydroxy-2-(1-imidazolylmethyl)-pyridine (6.0 g) in dry N,N-dimethylformamide (100 ml) was cooled to 5° C. and stirred under nitrogen. Sodium hydride (1.8 g as a dispersion in mineral oil) was added and the mixture was stirred for 1 hour at room temperature and then cooled to 0° C. A solution of 4-cyano-benzylbromide (6.8 g) in dry N,N-dimethylformamide (25 ml) was added and the mixture stirred at room temperature for a further 3 hours and allowed to stand overnight. Water (250 ml) was added and the aqueous solution extracted with ethyl acetate (4×100 ml). The organic extracts were combined, washed with water, dried over MgSO4 and evaporated to yield a solid. Recrystallization from ethyl acetate gave 3-(4-cyanobenzyloxy)-2-(1-imidazolylmethyl)pyridine (12.0 g), m.p. 159° C.

後処理

  1. stirringthe mixture was stirred for 1 hour at room temperature
  2. stirringthe mixture stirred at room temperature for a further 3 hours
  3. extractionthe aqueous solution extracted with ethyl acetate (4×100 ml)
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto yield a solid
  8. customRecrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-eb42d0a8ecfa4771861a1b15554e703d
出典データセット
uspto-grants-1982_07
特許番号
US04339583

反応ノート

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