Hydrochloric Acid → HCID 178427293, compound

HRID 1725118Notes

Reaction equation

HRID 1725118 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:13]=[C:12]([OH:14])[N:11]([CH3:15])[N:10]=1.[OH-].[Na+].[CH2:18]=O.[C:20]1([CH3:29])[CH:25]=[CH:24][C:23]([S:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([CH2:18][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:29])=[CH:21][CH:22]=2)(=[O:28])=[O:27])=[C:12]([OH:14])[N:11]([CH3:15])[N:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 2723791Sodium p-toluenesulfinateHCID 178481735HCID 178481735, compound

Product 1

HCID 178427293HCID 178427293, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-(2,4-Dichlorophenyl)-5-hydroxy-1-methylpyrazole (1.3 g (5 mmol)) synthesized in Reference Example 6 and 0.3 g (7.5 mmol) of sodium hydroxide were dissolved in 5 mL of ethanol. While stirring the resulting solution at room temperature, 1.0 g (11 mmol) of a 35% formalin solution was added dropwise thereto, followed by stirring at the same temperature for 1 hour. Subsequently, 0.9 g (5 mmol) of sodium p-toluenesulfinate was charged thereto at room temperature, and the obtained mixture was stirred for 2 hours. After the reaction, 2.5 g (25 mmol) of 35% hydrochloric acid was added dropwise thereto, 15 mL of water was further added, and the precipitated crystal was collected by filtration, washed twice with 10 mL of water and dried by a hot air drier to obtain 2.1 g (yield: 90.3%) of the title compound as a pale yellow crystal.

Workup

  1. stirringby stirring at the same temperature for 1 hour
  2. stirringat room temperature, and the obtained mixture was stirred for 2 hours
  3. additionwas added dropwise
  4. filtrationthe precipitated crystal was collected by filtration
  5. washwashed twice with 10 mL of water
  6. customdried by a hot air drier

Sources & evidence

ORD record
ord-68e6cd9d584143c7b9540d5fca4b52d2
Source dataset
uspto-grants-2009_02
Patent number
US07488831B2

Reaction notes

Loading…