Sodium hydride → N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide

HRID 1665003노트

반응식

HRID 1665003 반응식
[Br:1][C:2]1[S:6][C:5]([CH2:7][NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C(=O)C>[CH2:18]([N:8]([CH2:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:19])([F:21])[F:20])(=[O:11])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:12]=1

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 35408897N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide

생성물 1

HCID 67439229N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide수율 152.5%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

To a stirred solution of N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide (0.594 g) in N,N-dimethylacetamide (4 mL) was added NaH (dispersion, ca 55% in oil, 0.039 g) at 0° C. After stirring for 5 min, the ice bath was removed and the mixture was stirred for 50 min. Benzyl bromide (0.28 g) was added and the mixture was stirred overnight at r.t. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane to cyclohexane/ethyl acetate 2:1) to give N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide (0.555 g) as a colorless solid. MS: 490 ([M+H]+)

후처리

  1. customthe ice bath was removed
  2. stirringthe mixture was stirred for 50 min
  3. additionBenzyl bromide (0.28 g) was added
  4. stirringthe mixture was stirred overnight at r.t
  5. additionWater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe product was purified by chromatography (SiO2, cyclohexane to cyclohexane/ethyl acetate 2:1)

출처 및 근거

ORD 기록
ord-328568dcdb9d47c6862a7fad7772ac6e
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039493B2

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