Bromoacetonitrile → HCID 9880293、化合物

HRID 558257ノート

反応式

HRID 558257 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:9]([CH2:15][CH3:16])=[N:10][NH:11][C:12]=1[CH2:13][CH3:14].[H][H].Br[CH2:24][C:25]#[N:26]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:12]([CH2:13][CH3:14])=[N:11][N:10]([CH2:24][C:25]#[N:26])[C:9]=1[CH2:15][CH3:16]

参加物

6

反応物 4

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 9878953HCID 9878953、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 9880293HCID 9880293、化合物収率 94%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Sodium hydride (60% dispersion in oil, 470 mg, 11.8 mmol) was added to a stirred solution of 4-(3,5-dichlorophenoxy)-3,5-diethyl-1H-pyrazole (3 g, 10.5 mmol, Example 3) in dry N,N-dimethylformamide (20 ml) at 0° C. under nitrogen. The mixture was stirred for 5 minutes during which time hydrogen was evolved and then bromoacetonitrile (0.81 ml, 11.6 mmol) was added. The yellow solution turned dark brown and a precipitate formed. Further dry N,N-dimethylformamide (5 ml) was added to aid dissolution and after 45 minutes the reaction mixture was quenched by the addition of water (1 ml). The mixture was partitioned between water (150 ml) and diethyl ether (2×150 ml). The combined organic layers were washed with water (50 ml) and brine (100 ml), dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane to provide the title compound (3.2 g) as a yellow powder, m.p. 70-72° C.

後処理

  1. customa precipitate formed
  2. customwas quenched by the addition of water (1 ml)
  3. customThe mixture was partitioned between water (150 ml) and diethyl ether (2×150 ml)
  4. washThe combined organic layers were washed with water (50 ml) and brine (100 ml)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane

出典と根拠

ORDレコード
ord-447a7349880949438751c2c67510ea88
出典データセット
uspto-grants-2011_11
特許番号
US08063044B2

反応ノート

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