Water → 4-fluoro-2-[N-methyl-N-(2,2,2-trifluoroacetyl)aminomethyl]benzenesulfonyl chloride

HRID 928030노트

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HRID 928030 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]([CH3:13])[C:7](=[O:12])[C:8]([F:11])([F:10])[F:9].[Cl:17][S:18](O)(=[O:20])=[O:19].O>ClCCCl>[F:1][C:2]1[CH:16]=[CH:15][C:14]([S:18]([Cl:17])(=[O:20])=[O:19])=[C:4]([CH2:5][N:6]([CH3:13])[C:7](=[O:12])[C:8]([F:10])([F:11])[F:9])[CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 627348703-fluoro-N-methyl-N-(trifluoroacetyl)benzylamine2회

생성물 1

HCID 867133484-fluoro-2-[N-methyl-N-(2,2,2-trifluoroacetyl)aminomethyl]benzenesulfonyl chloride

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
70 °C

실험 절차

A solution of 3-fluoro-N-methyl-N-(trifluoroacetyl)benzylamine (Intermediate 159, 0.497 g) in DCE (0.5 mL) was added to stirred, cooled chlorosulfonic acid (3 mL). The mixture was allowed to come up to room temperature and then heated at 70° C. for 3 hours. After cooling, the mixture was added carefully to a mixture of ice and water, then extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane with a gradient of 2.5-10% to give 4-fluoro-2-[N-methyl-N-(2,2,2-trifluoroacetyl)aminomethyl]-benzenesulfonyl chloride (0.21 g) as a clear oil.

후처리

  1. customto come up to room temperature
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and pentane with a gradient of 2.5-10%

출처 및 근거

ORD 기록
ord-cf5786486b444d1682152ce7cdb8fa3f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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