Ammonium Hydroxide → HCID 178503364, compound

HRID 1762102Notes

Reaction equation

HRID 1762102 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.Cl.[CH2:10]([N:17]1[CH2:22][CH2:21][C:20](=O)[CH:19]([C:24](OC)=O)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-:28].[NH4+]>C(O)(=O)C>[CH2:10]([N:17]1[CH2:22][C:21](=[O:28])[C:20]2[N:1]=[C:2]3[N:3]=[C:4]([S:7][CH3:8])[NH:5][N:6]3[CH2:24][C:19]=2[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 784713-(Methylthio)-1,2,4-triazol-5-amineHCID 107479Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride

Product 1

HCID 178503364HCID 178503364, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 39.05 g (0.3 mole) of 5-amino-3-methylthio-1H-1,2,4-triazole, 85.1 g (0.3 mole) of 1-benzyl-3-carbomethoxy-4-piperidone-hydrochloride and 125 ml of acetic acid is heated to boiling for 5.5 hours. The reaction mixture is cooled and 350 ml of concentrated ammonium hydroxide are added. The mixture is allowed to stand for 16 hours at room temperature, the precipitated crystals are filtered and washed with water. The product is heated to boiling in 300 ml of methanol for 15 minutes and filtered again. The product is dissolved in hot dimethyl formamide, precipitated by adding acetonitrile, filtered and washed with acetonitrile. Thus 53.6 g of 7-benzyl-2-methylthio-6,7,8,9-tetrahydro-pyrido[4,3-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one are obtained, yield 54%, m.p.: 245°-247° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. waitto stand for 16 hours at room temperature
  3. filtrationthe precipitated crystals are filtered
  4. washwashed with water
  5. temperatureThe product is heated
  6. waitto boiling in 300 ml of methanol for 15 minutes
  7. filtrationfiltered again
  8. dissolutionThe product is dissolved in hot dimethyl formamide
  9. customprecipitated
  10. additionby adding acetonitrile
  11. filtrationfiltered
  12. washwashed with acetonitrile

Sources & evidence

ORD record
ord-1d520c0ea63b4e0faa51fd0ab98bb297
Source dataset
uspto-grants-1989_05
Patent number
US04831029

Reaction notes

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