Methane → HCID 131715768、化合物

HRID 2231744ノート

反応式

HRID 2231744 の反応式
Cl.Cl[C:3]([C:5]1[CH:6]=[CH:7][N:8]2[C:12]=1[CH2:11][S:10][CH:9]2[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=O.[NH2:19][C:20]1[CH:21]=[C:22]([CH:32]=[CH:33][CH:34]=1)[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[CH:26]=1)=[O:24].C(N(CC)CC)C.C.[O:43]1CCOC[CH2:44]1>C(#N)C>[CH3:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[C:23]([C:22]1[CH:21]=[C:20]([NH:19][C:44]([CH2:3][C:5]2[CH:6]=[CH:7][N:8]3[C:12]=2[CH2:11][S:10][CH:9]3[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:43])[CH:34]=[CH:33][CH:32]=1)=[O:24]

参加物

7

反応物 5

HCID 297MethaneHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 199113037-chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochlorideHCID 21285570(3-Aminophenyl)(3-methylphenyl)methanone

生成物 1

HCID 131715768HCID 131715768、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
64 °C

実験手順

7-Chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (6 g) is added, at a temperature between 64° and 70° C., to a solution of 3-amino-3'-methylbenzophenone (4.25 g) and triethylamine (4.05 g) in dioxane (150 cc) which is heated to a temperature in the vicinity of 64° C., in the course of 5 minutes. The suspension obtained is heated, with stirring, at a temperature in the vicinity of 100° C. for 8 hours and then stirred at a temperature in the vicinity of 20° C. for 16 hours. The solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C. The residue is dissolved in methylene chloride (300 cc). The solution obtained is washed twice with distilled water (300 cc in total), twice with an aqueous 1N sodium hydroxide solution (300 cc in total) and twice with distilled water (300 cc in total) and then dried over anhydrous magnesium sulphate, treated with decolourizing charcoal (0.5 g), filtered and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C. A crude product (9 g) is thereby obtained, which is dissolved in boiling acetonitrile (75 cc). Decolourizing charcoal (0.5 g) is added to the solution obtained and the suspension is filtered in the heated state. The filtrate is cooled at a temperature in the vicinity of 10° C. for 3 hours. The crystals formed are separated by filtration, washed 3 times with acetonitrile cooled to a temperature in the vicinity of 4° C. (30 cc in total) and 3 times with diethyl ether (90 cc in total) and then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 20° C. in the presence of potassium hydroxide pellets. N-[3-(3-methylbenzoyl)phenyl]-3-(3-pyridyl)-1H, 3H-pyrrolo[1,2-c]thiazole-7-carboxyamide (2.4 g) in the form of beige-coloured crystals, m.p. 164° C., is thereby obtained.

後処理

  1. customThe suspension obtained
  2. temperatureis heated
  3. stirringstirred at a temperature in the vicinity of 20° C. for 16 hours
  4. customThe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C
  5. dissolutionThe residue is dissolved in methylene chloride (300 cc)
  6. customThe solution obtained
  7. washis washed twice with distilled water (300 cc in total), twice with an aqueous 1N sodium hydroxide solution (300 cc in total) and twice with distilled water (300 cc in total)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. additiontreated with decolourizing charcoal (0.5 g)
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C
  12. customA crude product (9 g) is thereby obtained
  13. dissolutionwhich is dissolved
  14. customobtained
  15. filtrationthe suspension is filtered in the heated state
  16. temperatureThe filtrate is cooled at a temperature in the vicinity of 10° C. for 3 hours
  17. customThe crystals formed
  18. customare separated by filtration
  19. washwashed 3 times with acetonitrile
  20. temperaturecooled to a temperature in the vicinity of 4° C. (30 cc in total) and 3 times with diethyl ether (90 cc in total)
  21. dry with materialdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 20° C. in the presence of potassium hydroxide pellets

出典と根拠

ORDレコード
ord-44b34705eb98415ebcfee64311752963
出典データセット
uspto-grants-1988_11
特許番号
US04783472

反応ノート

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