Sodium Hydroxide → 2,2-Difluoro-6-[(4,5-dimethoxy-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5-f]benzimidazole

HRID 845522ノート

反応式

HRID 845522 の反応式
[OH-].[Na+].[F:3][C:4]1([F:17])[O:16][C:7]2=[CH:8][C:9]3[NH:13][C:12]([SH:14])=[N:11][C:10]=3[CH:15]=[C:6]2[O:5]1.[Cl-].Cl[CH2:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][NH+:22]=1>C(O)C.O>[F:17][C:4]1([F:3])[O:16][C:7]2=[CH:8][C:9]3[NH:13][C:12]([S:14][CH2:20][C:21]4[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][N:22]=4)=[N:11][C:10]=3[CH:15]=[C:6]2[O:5]1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 201313622-Chloromethyl-4,5-dimethoxypyridinium chlorideHCID 178506005HCID 178506005、化合物

生成物 1

HCID 151635072,2-Difluoro-6-[(4,5-dimethoxy-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5-f]benzimidazole

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
20 °C

実験手順

6.3 ml of 1N sodium hydroxide solution are added dropwise to a solution, warmed to 50° C., of 0.69 g of 2,2-difluoro-5H-[1,3]-dioxolo[4,5-f]benzimidazole-6-thiol and 0.67 g of 2-chloromethyl-4,5-dimethoxypyridinium chloride in 9 ml of ethanol and 4 ml of water in the course of one minute. On cooling the clear reaction mixture to 20° C., a colorless precipitate separates out after a short time. The mixture is stirred at 20° C. for a further 5 hours and the precipitate is filtered off with suction over a suction filter, rinsed with 1N sodium hydroxide solution and water and dried to constant weight. The beige solid is dissolved in 10 ml of methylene chloride, insoluble constituents are filtered off, the filtrate is concentrated and the residue is made to crystallize by addition of diisopropyl ether after cooling. 1.02 g (90% of theory) of the title compound of m.p. 189°-191° C. are obtained.

後処理

  1. filtrationthe precipitate is filtered off with suction over a suction
  2. filtrationfilter
  3. washrinsed with 1N sodium hydroxide solution and water
  4. customdried to constant weight
  5. dissolutionThe beige solid is dissolved in 10 ml of methylene chloride
  6. filtrationinsoluble constituents are filtered off
  7. concentrationthe filtrate is concentrated
  8. customto crystallize by addition of diisopropyl ether
  9. temperatureafter cooling

出典と根拠

ORDレコード
ord-91ab30a450ac420ea1f1def09b6466cd
出典データセット
uspto-grants-1988_07
特許番号
US04758579

反応ノート

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