4-Chloro-3-methylbenzene-1-sulfonyl chloride → HCID 86606891, 화합물

HRID 419024

반응식

HRID 419024 반응식
[Br:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[CH3:10][C:11]1[CH:12]=[C:13]([S:18](Cl)(=[O:20])=[O:19])[CH:14]=[CH:15][C:16]=1[Cl:17]>N1C=CC=CC=1>[Br:1][C:2]1[C:7]([NH:8][S:18]([C:13]2[CH:14]=[CH:15][C:16]([Cl:17])=[C:11]([CH3:10])[CH:12]=2)(=[O:19])=[O:20])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 2210014-Chloro-3-methylbenzene-1-sulfonyl chlorideHCID 27696403-Amino-2-bromo-5-chloropyridine

생성물 1

HCID 86606891HCID 86606891, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a stirred solution of 2-bromo-5-chloro-pyridin-3-ylamine (4.12 g, 20 mmol) in anhydrous pyridine (100 mL) was added 3-methyl-4-chlorobenzenesulfonyl chloride (6.35 g, 26 mmol) and the progress of the reaction was followed by LCMS. The reaction mixture was stirred overnight (18 h), then concentrated to remove as much of the pyridine as possible. The residue was dissolved in THF and was stirred 18 h with aqueous sodium hydroxide (20 mL) in THF to cleave the bis-sulfonamide. The reaction mixture was subsequently neutralized with aqueous HCl and extracted with EtOAc; the organic phase was washed with water (2×100 mL), brine, and then dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using EtOAc-hexane to provide N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro-3-methyl-benzenesulfonamide as a white crystalline solid. MS m/z 397.1 (M+H).

후처리

  1. concentrationconcentrated
  2. customto remove as much of the pyridine as possible
  3. dissolutionThe residue was dissolved in THF
  4. stirringwas stirred 18 h with aqueous sodium hydroxide (20 mL) in THF
  5. extractionextracted with EtOAc
  6. washthe organic phase was washed with water (2×100 mL), brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-d7b683a7dafe4d749cce0363d76258ba
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093247B2

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