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

HRID 1528543노트

반응식

HRID 1528543 반응식
[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

참가 물질

6

반응물 4

HCID 8078CyclohexaneHCID 24408BromineHCID 66826467N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide2회HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 solution was extracted with diethyl ether, 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.

후처리

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

출처 및 근거

ORD 기록
ord-e89dd55e7be44057838763833ee02cc1
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090604B2

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