Tributylamine → HCID 178432402, compound

HRID 1986636Notes

Reaction equation

HRID 1986636 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[CH:7]1([CH:12]([C:18](=O)[CH3:19])[C:13](OCC)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CCCC)CCCC)CCC>[OH-].[Na+]>[CH3:19][C:18]1[C:12]([CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[C:13]([OH:14])[N:3]2[N:4]=[CH:5][N:6]=[C:2]2[N:1]=1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 17750296Ethyl 2-cyclopentyl-3-oxobutanoateHCID 178418311HCID 178418311, compound

Product 1

HCID 178432402HCID 178432402, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3-amino-1,2,4-triazole (14 g), ethyl 2-cyclopentyl-3-oxobutanoate (0.17 mol, Ex. 1) and tributylamine (50 ml) was heated at 180° C. for 6 hours. The reaction mixture was cooled to about 70° C., and aqueous NaOH solution (21 g in 200 ml of H2O) was then added and the solution was stirred for another 30 min. Following phase separation and extraction with diethyl ether, the aqueous phase was acidified with conc. HCl solution. The precipitate gave 19 g of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to about 70° C.
  2. customFollowing phase separation and extraction with diethyl ether

Sources & evidence

ORD record
ord-57d71b38b94e4789b7f567a5272e2cb5
Source dataset
uspto-grants-2009_06
Patent number
US07550471B2

Reaction notes

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