1-Pyrrolidinecarbonyl chloride → HCID 18415666, compound

HRID 990622Notes

Reaction equation

HRID 990622 reaction equation
[Br:1][C:2]([F:12])([F:11])[S:3]([C:6]1[N:10]=[CH:9][NH:8][N:7]=1)(=[O:5])=[O:4].[N:13]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1>N1C=CC=CC=1.O>[Br:1][C:2]([F:11])([F:12])[S:3]([C:6]1[N:10]=[CH:9][N:8]([C:18]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:19])[N:7]=1)(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 709371-Pyrrolidinecarbonyl chlorideHCID 178527384HCID 178527384, compound

Product 1

HCID 18415666HCID 18415666, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 0.12 g (0.45 mmol) 3-(bromodifluoromethylsulfonyl)-1,2,4-triazole, prepared as above, in 0.5 ml dry pyridine was added 0.07 g (0.54 mmol) pyrrolidine-1-carbonyl chloride and the mixture was agitated for 16 h at room temperature. The reaction mixture was then diluted with water and extracted with ether. The resulting organic layer was washed successively with dilute hydrochloric acid, water and saturated sodium bicarbonate solution, dried over MgSO4 and evaporated to give 0.1 g (65% yield) of the desired 3-(bromodifluoromethylsulfonyl)-1-(pyrrolidinocarbonyl)-1,2,4-triazole as a pale yellow oil: 1H NMR (CDCl3) δ(ppm) 9.1 (1H), 4.0 (2H), 3.7 (2H), 2.1 (4H).

Workup

  1. extractionextracted with ether
  2. washThe resulting organic layer was washed successively with dilute hydrochloric acid, water and saturated sodium bicarbonate solution
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-a74cd095b8f44040af0ebf32a095d114
Source dataset
uspto-grants-2002_10
Patent number
US06461997B1

Reaction notes

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