Tributylamine → HCID 178517495, compound

HRID 2251742Notes

Reaction equation

HRID 2251742 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH:10]([C:16]([O:18]CC)=O)[C:11]([O:13]CC)=O.C(N(CCCC)CCCC)CCC.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]([NH2:42])=[NH:41].[OH-].[Na+]>O.C(O)C>[OH:13][C:11]1[C:10]([C:3]2[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])=[C:16]([OH:18])[N:42]=[C:40]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=2)[N:41]=1

Participants

7

Reactant 4

HCID 7622TributylamineHCID 14798Sodium HydroxideHCID 556504PicolinimidamideHCID 2782662Propanedioic acid, 2-(2,4,6-trifluorophenyl)-, 1,3-diethyl ester

Product 1

HCID 178517495HCID 178517495, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

332 g (1.16 mol) of diethyl 2-(2,4,6-trifluorophenyl)malonate and 192 g (1.04 mol) of tributylamine were heated at 180° C. for eight hours together with 182 g (1.17 mol) of pyridine-2-carboxamidine. In the course of this, the ethanol produced was distilled off. The reaction mixture was then allowed to cool to 60-70° C. and was mixed with a solution of 116 g (2.89 mol) of sodium hydroxide in 1200 ml of water. After stirring for 30 min and cooling to approximately 20-25° C., the mixture was extracted with methyl tert-butyl ether (MTBE) and, after phase separation, the aqueous phase was acidified with 6N hydrochloric acid. After filtering off and drying, 180 g of the title compound were obtained.

Workup

  1. distillationwas distilled off
  2. temperaturecooling to approximately 20-25° C.
  3. extractionthe mixture was extracted with methyl tert-butyl ether (MTBE)
  4. customafter phase separation
  5. filtrationAfter filtering off
  6. customdrying

Sources & evidence

ORD record
ord-f868174b9d3e42cbb9b90d6cd7bd71e6
Source dataset
uspto-grants-2008_01
Patent number
US07320975B2

Reaction notes

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