Acetic Acid → HCID 178503363, compound

HRID 1762100Notes

Reaction equation

HRID 1762100 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.Cl.[CH2:10](N1CCC(C(OCC)=O)C(=O)C1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:29]([OH:32])(=O)[CH3:30].CC(C)=O.[N:37]1C=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH2:10]([CH:39]1[C:40]2[CH2:41][N:6]3[NH:5][C:4]([S:7][CH3:8])=[N:3][C:2]3=[N:1][C:30]=2[C:29](=[O:32])[NH:37][CH2:38]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 1049Pyridine2×HCID 784713-(Methylthio)-1,2,4-triazol-5-amineHCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride

Product 1

HCID 178503363HCID 178503363, compoundYield 91%

Procedure

A mixture of 39.05 g (0.3 mole) of 5-amino-3-methylthio-1H-1,2,4-triazole, 1-benzyl-4-carbethoxy-3-oxo-piperidine-hydrochloride and 110 ml of acetic acid is heated to boiling for 6.5 hours. The reaction mixture is allowed to stand overnight, the precipitate is filtered and washed with acetone. Thus 115.30 g of the crude product are obtained. The crude product is dissolved in 130 ml of hot pyridine, and to the pyridine solution 400 ml of acetone are added. The precipitated crystals are filtered, washed with acetone, the product is dissolved in 270 ml of pyridine and 1000 ml of acetone are added to the pyridine solution. The precipitated crystals are filtered and washed with acetone. Thus 89.3 g of the desired compound are obtained, yield 91%, m.p.: 232°-234° C.

Workup

  1. temperatureis heated
  2. waitto stand overnight
  3. filtrationthe precipitate is filtered
  4. washwashed with acetone
  5. customThus 115.30 g of the crude product are obtained
  6. filtrationThe precipitated crystals are filtered
  7. washwashed with acetone
  8. dissolutionthe product is dissolved in 270 ml of pyridine
  9. addition1000 ml of acetone are added to the pyridine solution
  10. filtrationThe precipitated crystals are filtered
  11. washwashed with acetone

Sources & evidence

ORD record
ord-3d7198b5a9e74a9da613b9aa5ed9ba07
Source dataset
uspto-grants-1989_05
Patent number
US04831029

Reaction notes

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