Formaldehyde → HCID 18448695, compound

HRID 1269378Notes

Reaction equation

HRID 1269378 reaction equation
[CH3:1][O-:2].[Na+].[CH:4]1[C:5]([C:26]([F:29])([F:28])[F:27])=[CH:6][C:7]([Cl:25])=[C:8]([N:11]2[N:15]=[C:14]([C:16]#[N:17])[C:13]([S+:18]([O-:23])[C:19]([F:22])([F:21])[F:20])=[C:12]2[NH2:24])[C:9]=1[Cl:10].C=O>CO>[C:16]([C:14]1[C:13]([S:18]([C:19]([F:22])([F:20])[F:21])=[O:23])=[C:12]([NH:24][CH2:1][OH:2])[N:11]([C:8]2[C:7]([Cl:25])=[CH:6][C:5]([C:26]([F:27])([F:29])[F:28])=[CH:4][C:9]=2[Cl:10])[N:15]=1)#[N:17]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10942334Sodium MethoxideHCID 178510672HCID 178510672, compound

Product 1

HCID 18448695HCID 18448695, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 equivalent of a sodium methylate (30% solution in methanol) was rapidly added to a suspension of 0.437 g of Fipronil and 1.4 equivalent of paraformaldehyde in 3 mL of methanol to provide the 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-hydroxymethylamino-4-trifluoromethylsulfinylpyrazole (Compound V) after 3 hour at 20° C. and 1 hour at 60° C. Then 1 equivalent of sodium borohydride was added to the medium which provide after classical extraction and chromatography separation the 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylamino-4-trifluoromethylsulfinylpyrazole (Compound I).

Sources & evidence

ORD record
ord-21ef441cff9646668d929df322691915
Source dataset
uspto-grants-2007_04
Patent number
US07199246B2

Reaction notes

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