Tributylamine → HCID 178439765, compound

HRID 969741Notes

Reaction equation

HRID 969741 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[CH:7]([CH:10]([C:16](OCC)=[O:17])[C:11](OCC)=[O:12])([CH3:9])[CH3:8].C(N(CCCC)CCCC)CCC>[OH-].[Na+]>[OH:12][C:11]1[C:10]([CH:7]([CH3:9])[CH3:8])=[C:16]([OH:17])[N:3]2[N:4]=[CH:5][N:6]=[C:2]2[N:1]=1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 12966Diethyl isopropylmalonateHCID 178418311HCID 178418311, compound

Product 1

HCID 178439765HCID 178439765, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 14 g (0.17 mol) of 3-amino-1,2,4-triazole, 34.3 g (0.17 mol) of diethyl 2-isopropylmalonate and 50 ml of tributylamine were stirred at 180° C. for 6 h. The reaction mixture was then cooled to 70° C., an aqueous solution of sodium hydroxide (21 g/200 ml of water) was added and the mixture was stirred for 30 min. The organic phase was separated and the aqueous phase was extracted with diethyl ether. The aqueous phase was then acidified using conc. hydrochloric acid and the resulting precipitate was collected by filtration. Drying gave 27 g (0.14 mol) of the title compound.

Workup

  1. temperatureThe reaction mixture was then cooled to 70° C.
  2. stirringthe mixture was stirred for 30 min
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with diethyl ether
  5. filtrationthe resulting precipitate was collected by filtration
  6. customDrying

Sources & evidence

ORD record
ord-35d7e504eb854eebb436708296df8afd
Source dataset
uspto-grants-2007_12
Patent number
US07307172B2

Reaction notes

Loading…