Triethylamine → 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime

HRID 2303446Notes

Reaction equation

HRID 2303446 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[S:21]([CH3:23])=[O:22].Cl.CN[OH:27].C(N(CC)CC)C>CO>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([CH:19]=[N:20][OH:27])[C:3]=1[S:21]([CH3:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77906N-methylhydroxylamine hydrochlorideHCID 10861895HCID 10861895, compound

Product 1

HCID 1363524165-amino-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oximeYield 33.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-amino-3-cyano 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole (1 g), methylhydroxylamine hydrochloride (0.26 g) and triethylamine (0.4 g) was stirred in methanol at ambient temperature for 2 hours, evaporated, washed (water) extracted with ethyl acetate to give 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime (0.35 g) as a white solid m.p. about 190° C. Compound 2 was prepared in a similar manner from fipronil.

Workup

  1. customevaporated
  2. washwashed (water)
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-9cdacdc667e64d24af8f9c82d3f17072
Source dataset
uspto-grants-2002_08
Patent number
US06432997B1

Reaction notes

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