Pyridine → N-(4-Bromo-l-methyl-5-pyrazolyl)-S,S-dimethylsulfilimine

HRID 1741263Notes

Reaction equation

HRID 1741263 reaction equation
[CH3:1][S:2][CH3:3].ClCl.[NH2:6][C:7]1[N:11]([CH3:12])[N:10]=[CH:9][C:8]=1[Br:13].N1C=CC=CC=1>ClCCl>[Br:13][C:8]1[CH:9]=[N:10][N:11]([CH3:12])[C:7]=1[N:6]=[S:2]([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1068Dimethyl SulfideHCID 24526ChlorineHCID 6003514-Bromo-1-methyl-1H-pyrazol-5-amine

Product 1

HCID 23303942N-(4-Bromo-l-methyl-5-pyrazolyl)-S,S-dimethylsulfilimine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.60 mL (8.2 mmol) of dimethyl sulfide in 30 mL of dichloromethane was cooled to -20° C. and 0.50 g (7.0 mmol) of chlorine was added through a sparge tube with cooling and stirring. Subsequently, 1.0 g (5.7 mmol) of 5-amino-4-bromo-l-methylpyrazole and then 1.0 g (12.7 mmol) of pyridine were added with cooling and stirring. A 2 mL aliquot of this mixture was removed and the light yellow solids present were collected by filtration and washed with deuteroacetonitrile.

Workup

  1. temperaturewith cooling
  2. temperaturewith cooling
  3. stirringstirring
  4. customA 2 mL aliquot of this mixture was removed
  5. filtrationthe light yellow solids present were collected by filtration
  6. washwashed with deuteroacetonitrile

Sources & evidence

ORD record
ord-a70216e9faf0426ea55ddb0fffc328a2
Source dataset
uspto-grants-1999_10
Patent number
US05973148

Reaction notes

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