O-Methylhydroxylamine hydrochloride → HCID 178502870, compound

HRID 989233Notes

Reaction equation

HRID 989233 reaction equation
CO[C:3]([C:5]1[C:9]([S:10]([CH3:12])=[O:11])=[C:8]([NH2:13])[N:7]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:6]=1)=[NH:4].Cl.[O:27]([NH2:29])[CH3:28]>CO>[NH2:13][C:8]1[N:7]([C:14]2[C:15]([Cl:25])=[CH:16][C:17]([C:21]([F:23])([F:24])[F:22])=[CH:18][C:19]=2[Cl:20])[N:6]=[C:5]([C:3](=[NH:4])[NH:29][O:27][CH3:28])[C:9]=1[S:10]([CH3:12])=[O:11]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 54383158HCID 54383158, compound

Product 1

HCID 178502870HCID 178502870, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboximidic acid methyl ester (1.0 g) in anhydrous methanol was added anhydrous methoxylamine hydrochloride (0.2 g). After 4 hours at 20° C., the mixture was evaporated and dichloromethane and water added. The organic layer was dried (MgSO4), evaporated and chromatographed on a florisil column, eluting with 3:1 dichloromethane/ethyl acetate to give 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-methoxy-4-methylsulfinyl-1H-pyrazole-3-carboximidamide(0.28 g), m.p.140-145° C. Compound 49. By proceeding in a similar manner the following compounds were prepared: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-methoxy-4-trifluoromethylsulfinyl-1H-pyrazole-3-carboximidamide, m.p.169-170° C. Compound 41; and 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N-hydroxy-4-trifluoromethylsulfinyl-1H-pyrazole-3-carboximidamide, m.p.222-224° C. Compound 40.

Workup

  1. customthe mixture was evaporated
  2. additiondichloromethane and water added
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customchromatographed on a florisil column
  6. washeluting with 3:1 dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-86b38d6586694c6b9cb59d1f3108e41b
Source dataset
uspto-grants-2003_10
Patent number
US06638956B2

Reaction notes

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