Pyridine → N-(5-bromo-2-pyridinyl)-S,S-dimethylsulfilimine

HRID 1953204Notes

Reaction equation

HRID 1953204 reaction equation
Br[C:2]1[CH:3]=N[N:5]([CH3:11])[C:6]=1[N:7]=[S:8]([CH3:10])[CH3:9].NC1N(C)N=C[C:14]=1[Br:19].N1C=CC=CC=1.ClS(C1N=C2N(C(OCC)=NC(F)=C2)N=1)(=O)=O>ClCCl>[Br:19][C:14]1[CH:3]=[CH:2][C:6]([N:7]=[S:8]([CH3:10])[CH3:9])=[N:5][CH:11]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6003514-Bromo-1-methyl-1H-pyrazol-5-amineHCID 109679322-Chlorosulfonyl-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidineHCID 23303942N-(4-Bromo-l-methyl-5-pyrazolyl)-S,S-dimethylsulfilimine

Product 1

HCID 23303923N-(5-bromo-2-pyridinyl)-S,S-dimethylsulfilimineYield 428.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A mixture containing about 53 mmol of N-(4-bromo-1-methyl-5-pyrazolyl)-S,S-dimethylsulfilimine in about 28 mL of dichloromethane solution prepared in Example 7 omitting the recovery step was cooled to -10° C. and 1.0 g (5.7 mmol) of 5-amino-4-bromo-1-methylpyrazole, 0.54 g (6.8 mmol) of pyridine, 11.8 mmol of 2-chlorosulfonyl-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine, and 5 mL of dichloromethane were added sequentially with stirring and cooling at about -10° C. The mixture was allowed to stir at ambient temperature for 2 days. The solids present were recovered by filtration, washed with a small amount of 2-propanol, and dried to obtain 5.7 g of the title compound as a white solid. A purer sample amounting to 4.6 g (26 percent of theory) was obtained dissolving this in dimethyl sulfoxide and then adding water to reprecipitate it.

Workup

  1. temperaturecooling at about -10° C
  2. stirringto stir at ambient temperature for 2 days
  3. filtrationThe solids present were recovered by filtration
  4. washwashed with a small amount of 2-propanol
  5. customdried

Sources & evidence

ORD record
ord-78a2384f222b48968f7414dc9eca18b9
Source dataset
uspto-grants-2000_09
Patent number
US06114580

Reaction notes

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