3,4-Dimethoxybenzenesulfonyl chloride → HCID 24994808, 화합물

HRID 1258622노트

반응식

HRID 1258622 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[C:10]([NH2:13])[N:9]=2)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24](Cl)(=[O:26])=[O:25])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>N1C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24]([NH:13][C:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[S:12][N:11]=2)(=[O:25])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

참가 물질

4

반응물 2

HCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 27947575-(4-Chlorophenyl)-1,2,4-thiadiazol-3-amine

생성물 1

HCID 24994808HCID 24994808, 화합물수율 46.6%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 5-(4-chlorophenyl)-1,2,4-thiadiazol-3-amine (423 mg, 2.0 mmol) in 10 mL of dry pyridine was added 529 mg (2.23 mmol) of 3,4-dimethoxybenzenesulfonyl chloride. The solution was stirred at room temperature under Argon. After 21 h, the pyridine was removed in vacuo and flashed off with toluene. The residue was partitioned between EtOAc and 1M NaOH. The organic phase was washed with 1M NaOH until no turbidity was observed on rectification of a small sample. The alkaline phase was made acidic (˜pH 3) with 1M HCl and extracted with EtOAc. EtOH was used in the second extraction to assist solubilizing the sulfonamide. After drying over Na2SO4, solvent was removed in vacuo. The crude crystalline product weighed 0.45 g. The crude product was taken up in 13 mL of hot HOAc, diluted with 7 mL of H2O and seeded to give white needles (384 mg) after collection by filtration, washing with H2O, and drying in vacuo. The product had mp 220-221° C.

후처리

  1. customthe pyridine was removed in vacuo
  2. customThe residue was partitioned between EtOAc and 1M NaOH
  3. washThe organic phase was washed with 1M NaOH until no turbidity
  4. extractionextracted with EtOAc
  5. extractionEtOH was used in the second extraction
  6. dry with materialAfter drying over Na2SO4, solvent
  7. customwas removed in vacuo
  8. additiondiluted with 7 mL of H2O

출처 및 근거

ORD 기록
ord-ae5eb72ab29043e99eaf62c31d0a8d33
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466182B2

반응 노트

불러오는 중…