Tributylamine → HCID 178517388, compound

HRID 2357872Notes

Reaction equation

HRID 2357872 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.C([O:9][C:10](=O)[CH:11]([C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[C:18]=1[F:25])[C:12](OCC)=[O:13])C.C(N(CCCC)CCCC)CCC>[OH-].[Na+]>[OH:9][C:10]1[C:11]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[C:18]=2[F:25])=[C:12]([OH:13])[N:3]2[N:4]=[CH:5][N:6]=[C:2]2[N:1]=1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 68637486HCID 68637486, compoundHCID 178418311HCID 178418311, compound

Product 1

HCID 178517388HCID 178517388, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3-amino-1,2,4-triazole (14 g), diethyl(2,3,5-trifluorophenyl)-malonate (0.17 mol, obtained from Ex. 1) and tributylamine (50 ml) was heated at 180° C. for six hours. The reaction mixture was cooled to about 70° C. After addition of aqueous sodium hydroxide (21 g/200 ml H2O) the reaction mixture was stirred for 30 minutes. After separation of the organic phase the aqueous phase was extracted with diethyl ether. The aqueous phase was acidified with concentrated hydrochloric acid. The precipitate was collected by filtration and dried to yield 43 g of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to about 70° C
  2. customAfter separation of the organic phase the aqueous phase
  3. extractionwas extracted with diethyl ether
  4. filtrationThe precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-188ccdc085d6488c9d5f450cebfd9730
Source dataset
uspto-grants-2010_07
Patent number
US07763622B2

Reaction notes

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