Water → 2-(4-Chlorophenyl)-1H-imidazo[4,5-b]pyridin-1-yl-2-propanone hydrochloride

HRID 2351654노트

반응식

HRID 2351654 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:20][C:21](=[O:23])[CH3:22].O>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:20][C:21](=[O:23])[CH3:22])[C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 178477971HCID 178477971, 화합물

생성물 1

HCID 143904342-(4-Chlorophenyl)-1H-imidazo[4,5-b]pyridin-1-yl-2-propanone hydrochloride

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine (2.29 g, 0.01 mole), was added to a suspension of sodium hydride (0.44 g of 60% of sodium hydride/oil, 0.01 mole, washed one with hexanes) in 50 ml of dimethylformamide. The mixture was heated to 70° C. for 1 hr before the addition of chloroacetone (0.93 g, 0.01 mole) at room temperature. The reaction mixture was stirred at room temperature overnight, then poured into 300 ml of water. The precipitate was collected by filtration, washed with water, and dried under high vacuum at 50° C. overnight. The solid was recrystallized from methanol-water and dried under high vacuum at 50° C. overnight. The solid was dissolved in methanol, treated with charcoal, and filtered through Celite to give a pale yellow filtrate. The filtrate was concentrated and diluted with water to initiate crystallization. The precipitate was collected by filtration, washed with water, and dried under high vacuum overnight. The solid was dissolved in isopropyl alcohol, acidified with ethereal hydrogen chloride, diluted with isopropyl ether, and seeded to initiate crystallization. The crystalline solid was collected by filtration, washed with isopropyl ether, and dried under high vacuum overnight to give 1.6 g, (50%), m.p. 220°-22° C.

후처리

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried under high vacuum at 50° C. overnight
  4. customThe solid was recrystallized from methanol-water
  5. customdried under high vacuum at 50° C. overnight
  6. dissolutionThe solid was dissolved in methanol
  7. additiontreated with charcoal
  8. filtrationfiltered through Celite
  9. customto give a pale yellow filtrate
  10. concentrationThe filtrate was concentrated
  11. additiondiluted with water
  12. customcrystallization
  13. filtrationThe precipitate was collected by filtration
  14. washwashed with water
  15. customdried under high vacuum overnight
  16. dissolutionThe solid was dissolved in isopropyl alcohol
  17. additiondiluted with isopropyl ether
  18. customcrystallization
  19. filtrationThe crystalline solid was collected by filtration
  20. washwashed with isopropyl ether
  21. customdried under high vacuum overnight
  22. customto give 1.6 g, (50%), m.p. 220°-22° C.

출처 및 근거

ORD 기록
ord-4dff19edb4824ca3990dff3b8bc08617
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04873251

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