Methane → HCID 53738460, compound

HRID 2231757Notes

Reaction equation

HRID 2231757 reaction equation
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].[C:19]([C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=1)[NH2:32])(=[O:28])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C>O1CCOCC1.C(#N)C>[C:19]([C:29]1[CH:30]=[C:31]([NH:32][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:33]=[CH:34][CH:35]=1)(=[O:28])[CH:20]=[CH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 199113037-chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochlorideHCID 53786780HCID 53786780, compound

Product 1

HCID 53738460HCID 53738460, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

7-Chloroformyl-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (8.8 g) is added, at a temperature between 60° and 75° C., to a solution of 3-cinnamoylaniline (6.57 g) and triethylamine (5.95 g) in dioxane (165 cc) which is heated to a temperature in the vicinity of 60° C., in the course of 10 minutes. The suspension obtained is heated, with stirring, at a temperature in the vicinity of 100° C. for 6 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 50° C. The residue is dissolved in methylene chloride (500 cc). The solution obtained is washed 4 times with distilled water (650 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 50° C. A crude product (13.5 g) is thereby obtained, which is dissolved in boiling acetonitrile (300 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 4° C. for 16 hours. The crystals formed are separated by filtration, washed 3 times with acetonitrile (60 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- cinnamoylphenyl)-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole -7-carboxamide (7.1 g) in the form of beige-coloured crystals, m.p. 190° C., is thereby obtained.

Workup

  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 50° C
  5. dissolutionThe residue is dissolved in methylene chloride (500 cc)
  6. customThe solution obtained
  7. washis washed 4 times with distilled water (650 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 50° C
  12. customA crude product (13.5 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 16 hours
  17. customThe crystals formed
  18. customare separated by filtration
  19. washwashed 3 times with acetonitrile (60 cc in total)
  20. 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

Sources & evidence

ORD record
ord-fe6e0ad019f54f359956fe037917798d
Source dataset
uspto-grants-1988_11
Patent number
US04783472

Reaction notes

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