Cyclohexane → 5-bromo-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide

HRID 2096014Notes

Reaction equation

HRID 2096014 reaction equation
[CH3:1][N:2]([CH3:15])[S:3]([N:6]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7]1)(=[O:5])=[O:4].C([Li])CCC.C1CCCCC1.[Br:27]Br>O1CCCC1>[Br:27][C:10]1[N:6]([S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4])[N:7]=[C:8]([C:11]([F:14])([F:12])[F:13])[CH:9]=1

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 24408BromineHCID 66826467N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide2×HCID 178418339Butyllithium

Product 1

HCID 687456085-bromo-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide (i.e. the product of Example 10, Step A) (4.25 g, 17.5 mmol) in tetrahydrofuran (50 mL) was cooled to −78° C., and then 2 M n-butyllithium in cyclohexane (10.0 mL, 20.0 mmol) was added dropwise. The reaction mixture was stirred a further 30 minutes, and then bromine (1.0 mL, 3.1 g, 18.7 mmol) was added dropwise. The reaction mixture was stirred for 10 minutes, warmed to room temperature, and quenched with brine (50 mL). The resulting mixture was extracted with diethyl ether, and the extract was dried (MgSO4), and concentrated under reduced pressure to give 6.77 g of title compound as a light yellow oil. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. stirringThe reaction mixture was stirred for 10 minutes
  2. customquenched with brine (50 mL)
  3. extractionThe resulting mixture was extracted with diethyl ether
  4. dry with materialthe extract was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-013a8bb106a6417f8743bdd78c1ca044
Source dataset
uspto-grants-2013_05
Patent number
US08449898B2

Reaction notes

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