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Ammonium Chloride → HCID 18005445, compound

HRID 989241
Notes
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Reaction equation

HRID 989241 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 74680(Ethylsulfonyl)etheneHCID 82127Potassium hydrideHCID 108618955-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-methylsulfinylpyrazole

Product 1

HCID 18005445HCID 18005445, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
3×

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-0adbf66a133a438da1bde4a173119796
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06638956B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes