Tributylamine → HCID 178432407, compound

HRID 1851163Notes

Reaction equation

HRID 1851163 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[F:8][C:9]1[CH:10]=[C:11]([CH:15]([C:21](OCC)=[O:22])[C:16](OCC)=[O:17])[CH:12]=[CH:13][CH:14]=1.C(N(CCCC)CCCC)CCC>[OH-].[Na+].O>[F:8][C:9]1[CH:10]=[C:11]([C:15]2[C:21]([OH:22])=[N:1][C:2]3[N:3]([N:4]=[C:5]([CH3:7])[N:6]=3)[C:16]=2[OH:17])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 7622TributylamineHCID 2346103-Amino-5-methyl-4H-1,2,4-triazoleHCID 12965551Diethyl (3-fluorophenyl)propanedioate

Product 1

HCID 178432407HCID 178432407, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

5 g (51.87 mmol) 3-Amino-5-methyl-1,2,4-triazole, 16.2 g (67.4 mmol) diethyl (3-fluorophenyl)malonate and 20.4 mL tributylamine are stirred at 180° C. over night. The mixture is diluted with 2N NaOH solution and water and extracted three times with methyl-tert. butylether. These organic extracts are discarded. The aqueous phase is acidified at 0° C. with concentrated HCl until pH 3. The white precipitate is collected by filtration, washed with water (4 L) and dried in vacuo at 50° C. 11.97 g (88.7%) of the product are obtained and are used without further purification.

Workup

  1. extractionextracted three times with methyl-tert. butylether
  2. customis acidified at 0° C. with concentrated HCl until pH 3
  3. filtrationThe white precipitate is collected by filtration
  4. washwashed with water (4 L)
  5. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-8f3ebf9e612a4a28a28a58bfe9f5fdfa
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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