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Water → 5-Amino-3-cyano-4-(2,5-dichlorofuran-3-yl)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

HRID 1108833
Notes
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Reaction equation

HRID 1108833 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[C:21]1[CH:25]=[CH:24][O:23][C:22]=1[Cl:26].[Cl:27]N1C(=O)CCC1=O.CCOCC.O>O1CCCC1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:15])[F:16])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1[CH:25]=[C:24]([Cl:27])[O:23][C:22]=1[Cl:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 31398ChlorosuccinimideHCID 221209155-Amino-4-(2-chlorofuran-3-yl)-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

Product 1

HCID 99556725-Amino-3-cyano-4-(2,5-dichlorofuran-3-yl)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-amino-4-(2-chlorofuran-3-yl)-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (0.15 g) in tetrahydrofuran (7 ml) was added N-chlorosuccinimide (0.048 g). The mixture was left at room temperature for 24 hours and then heated at 50° C. for 3 hours and then left at room temperature for 96 hours. The reaction mixture was poured into ether (25 ml) and water (25 ml). The organic layer was washed with water (25 ml), then dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (10 g) eluted with hexane:dichloromethane (50:50). Combination and evaporation of suitable fractions gave the title compound as a white solid, m.p. 193-194° C.

Workup

  1. waitleft at room temperature for 96 hours
  2. washThe organic layer was washed with water (25 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (10 g)
  6. washeluted with hexane:dichloromethane (50:50)
  7. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-0eb4b0ac931c497c9e06232bb985f4df
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06069157

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes