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

HRID 420893Notes

Reaction equation

HRID 420893 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]=O.BrN1C(=O)CCC1=O.[CH2:31]([SH:34])[CH2:32][SH:33].[OH-].[Na+]>ClCCl>[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:34][CH2:31][CH2:32][S:33]1

Participants

6

Reactant 4

HCID 109021,2-EthanedithiolHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 193564785-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-formylpyrazole

Product 1

HCID 116904045-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-1H-pyrazole-3-carbonitrileYield 120.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-formyl-1H-pyrazole-3-carbonitrile (5.00 g, 13.7 mmol) in dichloromethane (100 mL) at room temperature was added N-bromosuccinimide (0.74 g, 4.1 mmol) followed by 1,2-ethanedithiol (1.98 g, 20.6 mmol). The resulting mixture was stirred at room temperature for 3.7 hr. It was then worked up by adding 2 N sodium hydroxide. The layers were separated and the organic layer was washed with brine and then dried (sodium sulfate). It was then concentrated to afford a light beige solid (7.0 g). 19F-NMR: −63.791.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationIt was then concentrated

Sources & evidence

ORD record
ord-1278f4fe27ed410cb9a7337bbb7becc9
Source dataset
uspto-grants-2012_01
Patent number
US08097732B2

Reaction notes

Loading…