4-Chloro-3-methylbenzene-1-sulfonyl chloride → HCID 86606891、化合物

HRID 419024

反応式

HRID 419024 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 86606891HCID 86606891、化合物

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d7b683a7dafe4d749cce0363d76258ba
出典データセット
uspto-grants-2012_01
特許番号
US08093247B2

関連ノート

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