Triethylamine → HCID 178504610, compound

HRID 989235Notes

Reaction equation

HRID 989235 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12](Cl)=[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].[ClH:24].[NH2:25][OH:26].C(N(CC)CC)C>CO>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:24])=[CH:11][C:10]([C:14]([F:15])([F:17])[F:16])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19](=[NH:20])[NH:25][OH:26])[C:3]=1[S:21]([CH3:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 10861895HCID 10861895, compound

Product 1

HCID 178504610HCID 178504610, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylsulfinylpyrazole (20 g) in methanol (120 ml) was added hydroxylamine hydrochloride (3.99 g), followed by addition of triethylamine (8.0 ml). The mixture was stirred at room temperature overnight then evaporated. The residue was partitioned between water and ethyl acetate. The organic layer was washed with water, followed by wash with brine. The organic layer was dried over anhydrous sodium sulfate. The solution was concentrated by evaporation of solvent. A precipitate was formed and collected by filtration. The solid was washed with small amount of ethyl acetate to give Compound 44 (16.1 g), m.p. 225-226° C.

Workup

  1. customthen evaporated
  2. customThe residue was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with water
  4. washby wash with brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationThe solution was concentrated by evaporation of solvent
  7. customA precipitate was formed
  8. filtrationcollected by filtration
  9. washThe solid was washed with small amount of ethyl acetate

Sources & evidence

ORD record
ord-c0b0f42a739744e9a8badaf00c941054
Source dataset
uspto-grants-2003_10
Patent number
US06638956B2

Reaction notes

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