Dimethylformamide → 4-(Pyridin-4-yloxy)benzene-1-sulfonyl chloride hydrochloride

HRID 1602978ノート

反応式

HRID 1602978 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([OH:17])(=O)=[O:15])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.CN(C)C=O.S(Cl)([Cl:25])=O>C(#N)C>[ClH:25].[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([Cl:25])(=[O:17])=[O:15])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27604974-(4-Pyridinyloxy)benzenesulfonic acid

生成物 1

HCID 27352574-(Pyridin-4-yloxy)benzene-1-sulfonyl chloride hydrochloride

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
75 °C

実験手順

To a suspension of 4-(pyrid-4-yl)oxybenzenesulfonic acid (1.3 kg) in acetonitrile (8 L), was added N,N-dimethylformamide (12.35 mL), and the viscous reaction mixture was heated to 75° C. Thionyl chloride (756 mL) was added to the reaction mixture over 30 minutes. The reaction mixture slowly became less viscous and became homogeneous after 45 minutes, which indicated the reaction was complete. A portion of the solvent (4 L) was evaporated under vacuum and tert-butyl methyl ether (4 L) was added. The resulting slurry was filtered under inert atmosphere. The filter cake was rinsed with tert-butyl methyl ether (2 L) and the solid dried under vacuum to yield 4-(pyrid-4-yl)oxybenzenesulfonyl chloride hydrochloride (1.35 kg) as a hygroscopic, off-white solid of pearlescent flakes: mp 182° C.; 1H NMR (CDCl3): δ 8.87 (d, J=7 Hz, 2H), 8.24 (d, J=8.5 Hz, 2H), 7.50 (d, J=8.5 Hz, 2H), 7.43 (d, J=7 Hz, 2H).

後処理

  1. customA portion of the solvent (4 L) was evaporated under vacuum and tert-butyl methyl ether (4 L)
  2. additionwas added
  3. filtrationThe resulting slurry was filtered under inert atmosphere
  4. washThe filter cake was rinsed with tert-butyl methyl ether (2 L)
  5. customthe solid dried under vacuum

出典と根拠

ORDレコード
ord-f0e87c5df0af4b8ab7bfb4f3894fb161
出典データセット
uspto-grants-1999_11
特許番号
US05985900

反応ノート

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