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

HRID 1602978노트

반응식

HRID 1602978 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f0e87c5df0af4b8ab7bfb4f3894fb161
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05985900

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