Tributylamine → HCID 178517336, compound

HRID 1267030Notes

Reaction equation

HRID 1267030 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[C:9]=1[CH:16]([C:22](OCC)=[O:23])[C:17](OCC)=[O:18].C(N(CCCC)CCCC)CCC>[OH-].[Na+]>[OH:18][C:17]1[C:16]([C:9]2[C:10]([F:15])=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[F:7])=[C:22]([OH:23])[N:3]2[N:4]=[CH:5][CH:6]=[C:2]2[N:1]=1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 2782662Propanedioic acid, 2-(2,4,6-trifluorophenyl)-, 1,3-diethyl esterHCID 178418806HCID 178418806, compound

Product 1

HCID 178517336HCID 178517336, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 3-amino-pyrazole (0.06 mol), diethyl (2,4,6-trifluorophenyl)-malonate (0.06 mol, obtained from Example 1) and tributylamine (30 ml) was heated with reflux at 175° C. for four hours. The reaction mixture was cooled to 100° C. Aqueous sodium hydroxide (10.3 g/120 ml H2O) was added and the reaction mixture was stirred for 30 min. and cooled to ambient temperature. The organic Phase was separated off and the aqueous Phase was extracted with diethylether. The aqueous Phase was acidified with concentrated hydrochloric acid. The precipitate was collected by filtration and dried to yield 15.7 g (93 %) of the pale yellow product having a melting point of 280° C.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to 100° C
  3. temperaturecooled to ambient temperature
  4. customThe organic Phase was separated off
  5. extractionthe aqueous Phase was extracted with diethylether
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-886459e8725c4347b987fb674e3d1a5b
Source dataset
uspto-grants-2003_04
Patent number
US06552026B2

Reaction notes

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