1,3-Dichloroacetone → 6-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridine

HRID 322294

反応式

HRID 322294 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Cl:9][CH2:10][C:11]([CH2:13]Cl)=O>COCCOC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:13]=[C:11]([CH2:10][Cl:9])[N:1]=2)[CH:4]=1

参加物

4

反応物 2

HCID 107931,3-DichloroacetoneHCID 706222-Amino-5-bromopyridine

生成物 1

HCID 116228946-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridine収率 10.4%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 2-amino-5-bromopyridine (10.0 g). 1,3-dichloroacetone (7.71 g) and 1,2-dimethoxyethane (40 ml) was stirred at room temperature for 4 hours. The precipitated crystals were collected by filtration, to which ethanol (100 ml) was added and heated under reflux. The reaction mixture was concentrated, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give crystals of 6-bromo-2-chloromethylimidazo-[1,2-a]pyridine (1.48 g, 10%). Recrystallization from ethyl acetate-hexane gave colorless needles, mp 129-130° C.

後処理

  1. filtrationThe precipitated crystals were collected by filtration, to which ethanol (100 ml)
  2. additionwas added
  3. temperatureheated
  4. temperatureunder reflux
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with saturated aqueous sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fb4cf1708f384c6ea2674a91b781cbde
出典データセット
uspto-grants-2001_04
特許番号
US06211215B1

関連ノート

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