Tributylamine → HCID 178517355, compound

HRID 1851167Notes

Reaction equation

HRID 1851167 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH2:9])[N:5]=2)[CH2:3][CH2:2]1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19])=[CH:13][CH:12]=1.C(N(CCCC)CCCC)CCC>[OH-].[Na+].O>[CH:1]1([C:4]2[N:5]=[C:6]3[N:9]=[C:23]([OH:24])[C:17]([C:14]4[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=4)=[C:18]([OH:19])[N:7]3[N:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 7622TributylamineHCID 27580175-cyclopropyl-1H-1,2,4-triazol-3-amineHCID 2782660Diethyl 2-(4-fluorophenyl)malonate

Product 1

HCID 178517355HCID 178517355, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

10.2 g (81.9 mmol) 5-Cyclopropyl-1,2,4-triazole-3-ylamine, 25 g (98.3 mmol) diethyl (4-fluorophenyl)malonate and 32.2 mL (135.2 mmol) tributylamine are stirred at 180° C. for 18 hours. The solution is diluted with 120 mL 2N NaOH solution and 120 mL water and the resulting mixture is extracted three times with methyl-tert. butylether. These organic extracts are discarded. The aqueous phase is acidified to pH 1 with 2N HCl. The precipitate is collected by filtration, washed with plenty of water and dried. This material (13.5 g=57.6%) is used without further purification.

Workup

  1. extractionthe resulting mixture is extracted three times with methyl-tert. butylether
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with plenty of water
  4. customdried
  5. customThis material (13.5 g=57.6%) is used without further purification

Sources & evidence

ORD record
ord-fa1f37a06f3c44758728100ce1a820d8
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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