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

HRID 2301716노트

반응식

HRID 2301716 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)oxy]benzenesulfonic acid 3a (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)oxy]benzenesulfonyl chloride hydrochloride 4a (1.35 kg) as a fluffy off-white solid of pearlescent flakes: mp 182° C.; 1H NMR (300 MHz, 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-aaaabc4429124413a9f4665354460baf
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06500948B1

반응 노트

불러오는 중…