Ammonium Chloride → HCID 18005445, compound

HRID 2288040Notes

Reaction equation

HRID 2288040 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].[H-].[K+].[CH2:26]([S:28]([CH:31]=[CH2:32])(=[O:30])=[O:29])[CH3:27].[Cl-].[NH4+]>CN(C=O)C>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([NH:1][CH2:27][CH2:26][S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])=[C:3]([S:21]([CH3:23])=[O:22])[C:4]([C:19]#[N:20])=[N:5]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 74680(Ethylsulfonyl)etheneHCID 82127Potassium hydrideHCID 10861895HCID 10861895, compound

Product 1

HCID 18005445HCID 18005445, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-methylsulfinylpyrazole (10 g) in dry DMF was added during 10 minutes to potassium hydride (0.7 g of a 35% suspension in oil) in dry DMF at 4° C. and stirred for 20 min. Vinyl ethyl sulfone (3.13 g) in dry DMF was added over 5hr at 4° C. and the mixture stirred overnight whilst warming to 20° C. under a nitrogen atmosphere. The mixture was recooled, ammonium chloride solution added and the organic layer washed (water), dried (sodium sulfate) and evaporated. The residue was crystallized (ethyl acetate/hexane) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(2-ethylsulfonylethylamino)-4-methylsulfinylpyrazole (4.08 g), m.p. 131-132° C.

Workup

  1. stirringthe mixture stirred overnight
  2. washthe organic layer washed (water)
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. customThe residue was crystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-95ec4a58f6dc49be8d898c0540cecff7
Source dataset
uspto-grants-2000_07
Patent number
US06087387

Reaction notes

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