Sodium borohydride → 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbonitrile

HRID 420895Notes

Reaction equation

HRID 420895 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[CH:21]1[S:25][CH2:24][CH2:23][S:22]1.[CH2:26](OC=C)C.[BH4-].[Na+]>C(O)C.O.C(OCC)(=O)C>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([NH:1][CH3:26])=[C:3]([CH:21]2[S:22][CH2:23][CH2:24][S:25]2)[C:4]([C:19]#[N:20])=[N:5]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 866204735-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-1H-pyrazole-3-carbonitrile ethoxyethylene

Product 1

HCID 231319151-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbonitrileYield 100%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-1H-pyrazole-3-carbonitrile-ethoxyethylene (1:1) (0.30 g, 0.6 mmol) in ethanol (40 mL) at 5 C was added sodium borohydride (74 mg, 1.9 mmol). The resulting mixture was stirred at room temperature for five hrs and then diluted with water and ethyl acetate. The layers were separated and the organic layer was washed with saturated sodium chloride, dried (Na2SO4), concentrated to afford a yellowish oil (0.27 g, 0.6 mmol); 19-F-NMR: −63.704.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with saturated sodium chloride
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-455c3442e3a44b99909c39b71e599e11
Source dataset
uspto-grants-2012_01
Patent number
US08097732B2

Reaction notes

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