Sodium ethoxide → HCID 178490013, compound

HRID 411573Notes

Reaction equation

HRID 411573 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([C:16]([F:19])([F:18])[F:17])[C:3]=1[C:20]([NH2:22])=[O:21].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:31][C:32](Cl)=O)[CH:28]=[CH:29][CH:30]=1.[O-]CC.[Na+]>C(O)C>[Cl:15][C:8]1[CH:9]=[C:10]([Cl:14])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]2=[N:1][C:32]([CH2:31][C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH3:23])[CH:26]=3)=[N:22][C:20](=[O:21])[C:3]2=[C:4]([C:16]([F:19])([F:18])[F:17])[NH:5]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 27332463-Methoxyphenylacetyl chlorideHCID 11360812HCID 11360812, compound

Product 1

HCID 178490013HCID 178490013, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 186 mg (0.50 mmol) of 5-amino-3-trifluoromethyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide in 6 mL of absolute ethanol was added 555 mg (3.0 mmol) of 3-methoxyphenylacetyl chloride followed by 2.26 mL (6.0 mmol) of 2.66 M sodium ethoxide in ethanol. The solution was stirred 23 h at reflux, and the heating mantle was then removed. The reaction was treated with 10 mL of 10% aq. HOAc, cooled to ambient temperature, and filtered. The filtrate was washed with 6 mL of 1:1 water-methanol then 6 mL of 1:3 ether-hexanes. The off-white solid was briefly air-dried to give 230 mg (91%) of 1-(2,4,6-trichlorophenyl)-3-trifluoromethyl-6-(3-methoxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one. Mass spec.: 503(M+H)+.

Workup

  1. temperatureat reflux
  2. customthe heating mantle was then removed
  3. additionThe reaction was treated with 10 mL of 10% aq. HOAc
  4. filtrationfiltered
  5. washThe filtrate was washed with 6 mL of 1:1 water-methanol
  6. customThe off-white solid was briefly air-dried

Sources & evidence

ORD record
ord-69b8f3318a524f618622a215d4e217d5
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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