Water → HCID 13565360、化合物

HRID 1589458

反応式

HRID 1589458 の反応式
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1.CCOCC.O.[NH2:20][CH:21]([CH3:24])[CH2:22]O>>[CH3:24][CH:21]1[N:20]2[N:4]=[C:5]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)[CH:6]=[CH:7][C:2]2=[N:3][CH2:22]1

参加物

5

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 51262-AminopropanolHCID 167324353-Chloro-6-(pyridin-3-yl)pyridazine

生成物 1

HCID 13565360HCID 13565360、化合物

実験手順

A 4.0 g sample of 3-chloro-6-(3-pyridinyl)pyridazine in 56 ml of 2-amino-1-propanol was heated at 140° C. for 8 hours. The solution was cooled, then poured into a mixture comprised of 200 ml of ether and 300 ml of water. The water layer was concentrated under vacuum and the 2-amino-1-propanol was removed by bulb to bulb distillation under high vacuum. The residue in 50 ml of thionyl chloride was refluxed for 0.5 hours then the volatiles were removed in vacuo. To the residue was added 150 ml of ethanol and 5 g of potassium carbonate. The mixture was refluxed for 4 hours. The solvent was evaporated in vacuo and the residue was partitioned between dichloromethane and water. The aqueous layer was extracted with three 50 ml portions of dichloromethane. The combined organic layers were dried over magnesium sulfate and the solvent was removed in vacuo. Ether was added to the residue and a brown solid was removed by filtration. The addition of hexane to the filtrate on chilling gave crystals which were recrystallized from ether-hexane to give 1.2 g of 2,3-dihydro-3-methyl-6-(3-pyridinyl)imidazo[1,2-b]pyridazine as orange crystals, mp 103.5°-105° C.

後処理

  1. temperatureThe solution was cooled
  2. additionpoured into a mixture
  3. concentrationThe water layer was concentrated under vacuum
  4. customthe 2-amino-1-propanol was removed by bulb to bulb distillation under high vacuum
  5. temperatureThe residue in 50 ml of thionyl chloride was refluxed for 0.5 hours
  6. customthe volatiles were removed in vacuo
  7. additionTo the residue was added 150 ml of ethanol and 5 g of potassium carbonate
  8. temperatureThe mixture was refluxed for 4 hours
  9. customThe solvent was evaporated in vacuo
  10. customthe residue was partitioned between dichloromethane and water
  11. extractionThe aqueous layer was extracted with three 50 ml portions of dichloromethane
  12. dry with materialThe combined organic layers were dried over magnesium sulfate
  13. customthe solvent was removed in vacuo
  14. additionEther was added to the residue
  15. customa brown solid was removed by filtration
  16. additionThe addition of hexane to the filtrate
  17. temperatureon chilling
  18. customgave crystals which
  19. customwere recrystallized from ether-hexane

出典と根拠

ORDレコード
ord-a37aeefd88bb412cb3449093290f289c
出典データセット
uspto-grants-1986_02
特許番号
US04569934

関連ノート

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