Acetic Acid → HCID 53912360, compound

HRID 2231759Notes

Reaction equation

HRID 2231759 reaction equation
C([O:3][C:4]([C:6]1[CH:36]=[CH:35][CH:34]=[CH:33][C:7]=1[C:8]([C:10]1[CH:11]=[C:12]([NH:16][C:17]([C:19]2[CH:20]=[CH:21][N:22]3[C:26]=2[CH2:25][S:24][CH:23]3[C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:18])[CH:13]=[CH:14][CH:15]=1)=[O:9])=[O:5])C.[OH-].[K+].C(O)(=O)C.C>C(O)C.C(O)CCC.CN(C)C=O>[C:4]([C:6]1[CH:36]=[CH:35][CH:34]=[CH:33][C:7]=1[C:8]([C:10]1[CH:11]=[C:12]([NH:16][C:17]([C:19]2[CH:20]=[CH:21][N:22]3[C:26]=2[CH2:25][S:24][CH:23]3[C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:18])[CH:13]=[CH:14][CH:15]=1)=[O:9])([OH:5])=[O:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 297MethaneHCID 14797Potassium HydroxideHCID 21285567HCID 21285567, compound

Product 1

HCID 53912360HCID 53912360, compoundYield 43.4%

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of N-[3-(2-ethoxycarbonylbenzoyl)phenyl]- 3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide (4.4 g) and potassium hydroxide pellets (1.8 g) in a mixture of ethanol (100 cc) and distilled water (50 cc) is stirred at a temperature in the vicinity of 20° C. for 3 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 distilled water (350 cc) and the solution obtained is adjusted to a pH in the region of 4 by adding an aqueous 4N acetic acid solution. The crystals formed are separated by filtration, washed 5 times with distilled water (500 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. A crude product (3.5 g) is thereby obtained, which is dissolved in a boiling mixture (200 cc) of butan-1-ol and dimethylformamide (35:65 by volume). 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 3 days. The crystals formed are separated by filtration, washed 3 times with a mixture (30 cc in total) of butan-1-ol and dimethylformamide (35:65 by volume), 3 times with ethanol (90 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-(2-carboxybenzoyl) phenyl]-3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide (1.8 g) in the form of white crystals, m.p. 315° C. is thereby obtained.

Workup

  1. distillationdistilled water (50 cc)
  2. customThe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature in the vicinity of 60° C
  3. dissolutionThe residue is dissolved in distilled water (350 cc)
  4. customthe solution obtained
  5. customThe crystals formed
  6. customare separated by filtration
  7. washwashed 5 times with distilled water (500 cc in total)
  8. 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
  9. customA crude product (3.5 g) is thereby obtained
  10. customobtained
  11. filtrationthe suspension is filtered in the heated state
  12. temperatureThe filtrate is cooled at a temperature in the vicinity of 4° C. for 3 days
  13. customThe crystals formed
  14. customare separated by filtration
  15. washwashed 3 times with a mixture (30 cc in total) of butan-1-ol and dimethylformamide (35:65 by volume), 3 times with ethanol (90 cc in total) and 3 times with diethyl ether (90 cc in total)
  16. 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-5cf181c336524e95a563257ed109e815
Source dataset
uspto-grants-1988_11
Patent number
US04783472

Reaction notes

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