Thiabendazole → 1-(2-Benzyloxyethoxycarbonyl)-2-(4-thiazolyl)-benzimidazole

HRID 328333

反応式

HRID 328333 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12](Cl)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:15]1[CH:19]=[C:18]([C:20]2[NH:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[N:17]=[CH:16]1.Cl.N1C=CC=CC=1>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]([N:24]1[C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[N:21]=[C:20]1[C:18]1[N:17]=[CH:16][S:15][CH:19]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 5430ThiabendazoleHCID 45639002-Benzyloxyethyl chloroformateHCID 10176127Pyridinium chloride

生成物 1

HCID 214417221-(2-Benzyloxyethoxycarbonyl)-2-(4-thiazolyl)-benzimidazole

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

32.2 G. (150 mmoles) of 2-benzyloxyethylchloroformate is added dropwise with protection from moisture to a stirred suspension of 30.1 g. (150 mmoles) of 2(4-thiazolyl)-benzimidazole in 200 ml. of pyridine. The addition is complete in 30 minutes whereupon all of the starting material is dissolved and pyridine hydrochloride begins to precipitate. The reaction mixture is stirred at room temperature for 15 1/2 hours and filtered to remove pyridine hydrochloride. The solid material is washed with a small volume of pyridine and the combined filtrate and washing are evaporated to dryness in vacuo. The residual oil is dissolved in 300 ml. of methylene chloride and allowed to stand during which time a substantial amount of solid material precipitates. The solid is removed by filtration and the filtrate washed twice with 250 ml. of 0.25 N HCl containing ice followed by 200 ml. of saturated sodium bicarbonate solution containing 50 ml. of ice. The methylene chloride fraction is dried with magnesium sulfate, treated with charcoal, filtered and evaporated to dryness in vacuo affording 38.9 g. of a yellow-orange oil which begins to solidify on standing. The material is recrystallized from toluenecyclohexane affording 23.8 g. of 1-(2-benzyloxyethoxycarbonyl)-2-(4-thiazolyl)-benzimidazole, m.p. 93°-95° C.

後処理

  1. additionThe addition
  2. dissolutionwhereupon all of the starting material is dissolved
  3. customto precipitate
  4. filtrationfiltered
  5. customto remove pyridine hydrochloride
  6. washThe solid material is washed with a small volume of pyridine
  7. washthe combined filtrate and washing
  8. customare evaporated to dryness in vacuo
  9. dissolutionThe residual oil is dissolved in 300 ml
  10. customprecipitates
  11. customThe solid is removed by filtration
  12. washthe filtrate washed twice with 250 ml
  13. additionof 0.25 N HCl containing ice
  14. additionof saturated sodium bicarbonate solution containing 50 ml
  15. dry with materialThe methylene chloride fraction is dried with magnesium sulfate
  16. additiontreated with charcoal
  17. filtrationfiltered
  18. customevaporated to dryness in vacuo
  19. customaffording 38.9 g
  20. customThe material is recrystallized from toluenecyclohexane affording 23.8 g

出典と根拠

ORDレコード
ord-179c30dd96af4d33bcc359b2436b5e89
出典データセット
uspto-grants-1977_04
特許番号
US04017503

関連ノート

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