Ammonium Chloride → HCID 18005445, compound

HRID 1700405Notes

Reaction equation

HRID 1700405 reaction equation
[H-].[K+].[NH2:3][C:4]1[N:8]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[N:7]=[C:6]([C:21]#[N:22])[C:5]=1[S:23]([CH3:25])=[O:24].[CH2:26]([S:28]([CH:31]=[CH2:32])(=[O:30])=[O:29])[CH3:27].[Cl-].[NH4+]>CN(C)C=O>[Cl:20][C:10]1[CH:11]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:13]=[C:14]([Cl:15])[C:9]=1[N:8]1[C:4]([NH:3][CH2:27][CH2:26][S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])=[C:5]([S:23]([CH3:25])=[O:24])[C:6]([C:21]#[N:22])=[N:7]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

To a suspension of 35% potassium hydride in oil (0.7 g) in dry N,N-dimethylformamide (DMF) was added a solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(methylsulfinyl)-1H-pyrazole-3-carbonitrile (10.0 g) in dry DMF dropwise at 4° C. over 10 minutes. After stirring for 20 minutes, vinyl ethyl sulfone (3.13 g) in dry DMF was added during 5 hours at 4° C. The mixture was stirred overnight under nitrogen with warming to 20° C. Ammonium chloride was added at 4° C., and the mixture extracted (ethyl acetate), washed twice with water, dried (sodium sulfate) and evaporated. Crystallization from ethyl acetate/methanol/hexane gave 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[2-(ethylsulfonyl)ethylamino]-4-(methylsulfinyl)-1H-pyrazole-3-carbonitrile (4.08 g), m.p. 131-132° C. By proceeding in a similar manner the following compounds were prepared:

Workup

  1. stirringThe mixture was stirred overnight under nitrogen
  2. extractionthe mixture extracted (ethyl acetate)
  3. washwashed twice with water
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customCrystallization from ethyl acetate/methanol/hexane

Sources & evidence

ORD record
ord-13a9d03b2cf34965a3644a283baf5170
Source dataset
uspto-grants-2002_02
Patent number
US06350771B1

Reaction notes

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