Tributylamine → HCID 178517358, compound

HRID 1851227Notes

Reaction equation

HRID 1851227 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][C:9]([NH2:12])=[N:10][N:11]=1.[C:13]1([CH:19]([C:25](OCC)=[O:26])[C:20](OCC)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CCCC)CCCC)CCC>O>[C:13]1([C:19]2[C:20]([OH:21])=[N:12][C:9]3[N:10]([N:11]=[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[N:8]=3)[C:25]=2[OH:26])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 66514Diethyl phenylmalonate2×HCID 178509138HCID 178509138, compound

Product 1

HCID 178517358HCID 178517358, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

20 g (124.1 mmol) 5-Pyridine-2-yl-4H-[1,2,4]triazole-3-ylamine and 52.8 g (223.4 mmol) diethyl phenylmalonate are heated in 48.8 mL (204.8 mmol) tributylamine at 180° C. over night. After addition of additional 27 mL diethyl phenylmalonate the reaction mixture is heated for another night at 180° C. The reaction mixture is diluted with water and 2N NAOH and extracted three times with methyl-tert.butylether. The organic extracts are discarded after TLC check. The aqueous phase is acidified with 2M HCl until a pH of 1. The formed precipitate is collected by filtration, washed with plenty of water and dried. 18.96 g (45%) of the desired product are obtained which are used in the next step without further purification.

Workup

  1. extractionextracted three times with methyl-tert.butylether
  2. filtrationThe formed precipitate is collected by filtration
  3. washwashed with plenty of water
  4. customdried

Sources & evidence

ORD record
ord-f9f2ee0c2d8446c889441ee3fc4e31ea
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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