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

HRID 420897Notes

Reaction equation

HRID 420897 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.[SH:31][CH2:32][CH2:33][CH2:34][SH:35].[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:35][CH2:34][CH2:33][CH2:32][S:31]1

Participants

6

Reactant 4

HCID 80131,3-PropanedithiolHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 193564785-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-formylpyrazole

Product 1

HCID 231319165-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithian-2-yl)-1H-pyrazole-3-carbonitrileYield 33%

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 (0.5 g, 1.4 mmol) in dichloromethane (10 mL) was added N-bromosuccinimide (0.075 g, 0.2 mmol) followed by the addition of 1,3-dimercaptopropane (0.19 g, 1.8 mmol). The resulting solution was stirred at room temperature for eight hours. It was then worked-up by the addition of 2 N sodium hydroxide. The layers were separated and the organic layer was dried (Na2SO4) and concentrated. The resulting solid was further purified via silica gel column eluting with heptane:ethyl acetate (1:1) to afford a white solid (0.2 g, 33%). 19F-NMR: −64.231.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe resulting solid was further purified via silica gel column
  5. washeluting with heptane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-c09af8d7191c4465b97c32d7fc432258
Source dataset
uspto-grants-2012_01
Patent number
US08097732B2

Reaction notes

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