Hydrochloric Acid → HCID 19973434、化合物

HRID 1452042ノート

反応式

HRID 1452042 の反応式
[Mg].BrCC.Br[C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([CH3:15])[N:14]=2)[CH:11]=1.[CH2:16]=[O:17].Cl>O1CCCC1.II>[CH3:15][C:13]1[N:14]=[C:9]2[CH:8]=[CH:7][C:6]([CH2:16][OH:17])=[CH:11][N:10]2[CH:12]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 712Formaldehyde2 回HCID 6332Ethyl Bromide2 回HCID 5462224MagnesiumHCID 124289606-Bromo-2-methylimidazo[1,2-a]pyridine

生成物 1

HCID 19973434HCID 19973434、化合物収率 91.9%

試薬・触媒・溶媒 2

HCID 807Iodine触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In a nitrogen atmosphere, 78.56 g of magnesium was added to 2 l of tetrahydrofuran and 0.3 g of iodine and 18 ml of bromoethane were added to the obtained mixture to prepare a Grignard reagent. A solution of 170.5 g of 6-bromo-2-methylimidazo[1,2-a]pyridine and 162 ml of bromoethane in 500 ml of tetrahydrofuran was slowly dropped into the above reaction mixture. After the completion of the dropping, the obtained mixture was heated under reflux for 30 minutes and then cooled with ice. Formaldehyde gas generated by heating a container containing 242 g of paraformaldehyde to 200° C. was introduced into the reaction mixture by the use of a nitrogen stream. After 30 minutes, dilute hydrochloric acid was added to the resulting mixture and the obtained mixture was filtered to remove insolubles. The filtrate was alkalinized with concentrated aqueous ammonia and extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (30:1 to 10:1)] to give 120 g of the title compound as a pale-yellow solid (yield: 91.9%).

後処理

  1. additionwere added to the obtained mixture
  2. temperatureAfter the completion of the dropping, the obtained mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. temperaturecooled with ice
  5. temperatureby heating a container
  6. additionwas introduced into the reaction mixture by the use of a nitrogen stream
  7. filtrationthe obtained mixture was filtered
  8. customto remove insolubles
  9. extractionextracted with chloroform
  10. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  11. distillationdistilled
  12. customto remove the solvent
  13. customThe residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (30:1 to 10:1)]

出典と根拠

ORDレコード
ord-29559e7c5f4c41a186cfca5243451495
出典データセット
uspto-grants-1997_02
特許番号
US05606061

反応ノート

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