Hydrochloric Acid → HCID 22909707, compound

HRID 1379103Notes

Reaction equation

HRID 1379103 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=3)=[CH:13][C:12]([C:25]([F:28])([F:27])[F:26])=[N:11]2)=[CH:6][CH:5]=1.[CH3:29][O:30][CH2:31]Cl.Cl>CN(C)C=O>[CH3:29][O:30][CH2:31][O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=3)=[CH:13][C:12]([C:25]([F:26])([F:27])[F:28])=[N:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 22909685HCID 22909685, compound

Product 1

HCID 22909707HCID 22909707, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.17 g) was added to a solution of 1-(4-hydroxyphenyl)-5-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)pyrazole (1.5 g) in N,N-dimethylformamide (15 ml) at 5° C. The mixture was stirred at ambient temperature for 30 minutes. To the mixture was added chloromethyl methyl ether (0.4 g) in N,N-dimethylformamide (2 ml) at 5° C. The obtained mixture was stirred at 5° C. for 2 hours and at ambient temperature for 1 hour, poured into a mixture of ice and dilute hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated. The residue (1.3 g) was recrystallized from isopropanol to give crystals of 1-[4-(methoxymethoxy)phenyl]-5-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)pyrazole (1.3 g).

Workup

  1. stirringThe obtained mixture was stirred at 5° C. for 2 hours and at ambient temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue (1.3 g) was recrystallized from isopropanol

Sources & evidence

ORD record
ord-257279f009a2437497fc55a7a6847124
Source dataset
uspto-grants-1997_09
Patent number
US05670533

Reaction notes

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