Sodium ethoxide → HCID 178490014, compound

HRID 411562Notes

Reaction equation

HRID 411562 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]([S:16][CH3:17])[C:3]=1[C:18]([NH2:20])=[O:19].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30](Cl)=O)[CH:26]=[CH:27][CH:28]=1.[O-]CC.[Na+]>C(O)C>[Cl:13][C:12]1[CH:11]=[C:10]([Cl:14])[CH:9]=[C:8]([Cl:15])[C:7]=1[N:6]1[C:2]2=[N:1][C:30]([CH2:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH3:21])[CH:24]=3)=[N:20][C:18](=[O:19])[C:3]2=[C:4]([S:16][CH3:17])[NH:5]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 27332463-Methoxyphenylacetyl chlorideHCID 113025915-Amino-3-(methylthio)-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide

Product 1

HCID 178490014HCID 178490014, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 176 mg (0.5 mmol) of 5-amino-3-(methylthio)-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide in 6 mL of absolute ethanol was added 550 mg (3.0 mmol) of 3-methoxyphenylacetyl chloride followed by 2.3 mL (6.0 mmol) of 2.66 M sodium ethoxide in ethanol. The solution was stirred 18 h at reflux, and the heating mantle was then removed. The reaction was treated with 5 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 1:1 ether-hexanes. The off-white solid was briefly air-dried to give 220 mg (92%) of 1-(2,4,6-trichlorophenyl)-3-(methylthio)-6-(3-methoxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one,

Workup

  1. temperatureat reflux
  2. customthe heating mantle was then removed
  3. additionThe reaction was treated with 5 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-46c14b8c49ad4d89a773860da83b0bc2
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

Loading…