Dimethyl acetylenedicarboxylate → HCID 44542635, compound

HRID 2194846Notes

Reaction equation

HRID 2194846 reaction equation
[C:1]([O:9]C)(=O)[C:2]#[C:3][C:4]([O:6][CH3:7])=[O:5].[F:11][C:12]([F:22])([F:21])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.C[O-].[Na+]>CCOCC>[O:9]=[C:1]1[N:19]([C:16]2[CH:17]=[CH:18][C:13]([C:12]([F:11])([F:22])[F:21])=[CH:14][CH:15]=2)[N:20]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH2:2]1

Participants

5

Reactant 3

HCID 12980Dimethyl acetylenedicarboxylateHCID 1362004-(Trifluoromethyl)phenylhydrazineHCID 10942334Sodium Methoxide

Product 1

HCID 44542635HCID 44542635, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 500 mL round-bottomed flask was charged with dimethyl but-2-ynedioate 70 (6.0 g, 42 mmol) and 50 mL of ether. To this solution was added a solution of 1-(4-(trifluoromethyl)phenyl)hydrazine 69 (7.6 g, 43 mmol) in 100 mL of ether over 30 min. After stirring at room temperature for 30 min, the reaction was concentrated and redissolved in MeOH (200 mL). The solution was added dropwise over 1 h to a NaOMe solution (made from sodium metal (3.9 g, 169 mmol) in 200 mL of MeOH). This mixture was stirred at room temperature for 1.5 h, the MeOH was removed, 100 mL of 5 N HCl was added, and the precipitate was collected by filtration. The solid was triturated with CH2Cl2 to give methyl 5-oxo-1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylate 71.

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutionredissolved in MeOH (200 mL)
  3. stirringThis mixture was stirred at room temperature for 1.5 h
  4. customthe MeOH was removed
  5. addition100 mL of 5 N HCl was added
  6. filtrationthe precipitate was collected by filtration
  7. customThe solid was triturated with CH2Cl2

Sources & evidence

ORD record
ord-e661afd20e1d490990dabefb0fc2ac88
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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