Tributylamine → HCID 178509618, compound

HRID 857926Notes

Reaction equation

HRID 857926 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:21](OCC)=[O:22])[C:16](OCC)=[O:17])=[CH:11][CH:10]=1)#[N:8].C(N(CCCC)CCCC)CCC.[OH-].[Na+]>O>[OH:17][C:16]1[C:15]([C:12]2[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][CH:11]=2)=[C:21]([OH:22])[N:3]2[N:4]=[CH:5][N:6]=[C:2]2[N:1]=1

Participants

6

Reactant 4

HCID 7622TributylamineHCID 14798Sodium HydroxideHCID 11737076Diethyl (4-cyanophenyl)propanedioateHCID 178418311HCID 178418311, compound

Product 1

HCID 178509618HCID 178509618, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 14 g of 3-amino-1,2,4-triazole, 0.17 mol of the ester from example 1 and 50 ml of tributylamine (50 ml) was stirred at 180° C. for approximately 6 hours. A solution of 21 g of NaOH in 200 ml of water was added at approximately 700 and the mixture was stirred for a further 30 min. The organic phase was separated and the aqueous phase was extracted with diethyl ether. The product precipitated from the aqueous phase after acidification with concentrated hydrochloric acid. 28 g of the title compound were obtained by filtration.

Workup

  1. stirringthe mixture was stirred for a further 30 min
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with diethyl ether
  4. customThe product precipitated from the aqueous phase after acidification with concentrated hydrochloric acid

Sources & evidence

ORD record
ord-35e276461e314910b85204b5b4f94f03
Source dataset
uspto-grants-2006_12
Patent number
US07148227B2

Reaction notes

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