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Methane → HCID 21284366, 화합물

HRID 2232071
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HRID 2232071 반응식
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:4].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=1.C(N(CC)CC)C.C>O1CCOCC1.C(#N)C>[CH3:26][C:22]1[N:21]=[C:20]([NH:19][C: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:4])[CH:25]=[CH:24][CH:23]=1
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참가 물질

7

반응물 4

HCID 297MethaneHCID 8471TriethylamineHCID 157652-Amino-6-methylpyridineHCID 199113037-chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride

생성물 1

HCID 21284366HCID 21284366, 화합물수율 37.3%

시약·촉매·용매 2

HCID 6342Acetonitrile
용매
HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

7-Chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (6 g) is added, at a temperature between 60° and 66° C., to a solution of 2-amino-6-picoline (2.2 g) and triethylamine (4.05 g) in dioxane (130 cc) which is heated to a temperature in the vicinity of 60° C., in the course of 5 minutes. The suspension obtained is heated, with stirring, at a temperature in the vicinity of 100° C. for 7 hours and 30 minutes 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) and the solution obtained is washed twice with distilled water (300 cc in total), twice with an aqueous 2N 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 decolorizing 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 (5.6 g) is thereby obtained, which is dissolved in boiling acetonitrile (60 cc). Decolorizing 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 4° C. for 2 hours. The crystals formed are separated by filtration, washed twice with acetonitrile cooled to a temperature in the vicinity of 4° C. (20 cc in total) and then twice with diethyl ether (50 cc in total) and 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-(6-methyl-2-pyridyl)-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide (2.5 g) in the form of beige-coloured crystals, m.p. 162° C., is thereby obtained.

후처리

  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 2N 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 decolorizing 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 (5.6 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 4° C. for 2 hours
  17. customThe crystals formed
  18. customare separated by filtration
  19. washwashed twice with acetonitrile
  20. temperaturecooled to a temperature in the vicinity of 4° C. (20 cc in total)
  21. dry with materialtwice with diethyl ether (50 cc in total) and 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

출처 및 근거

ORD 기록
ord-879f05b7b2bd4aca81dd30ecbce3686b
출처 데이터셋
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04786645

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