3,4-Dimethoxybenzenesulfonyl chloride → HCID 24994808、化合物

HRID 1258622ノート

反応式

HRID 1258622 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 24994808HCID 24994808、化合物収率 46.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ae5eb72ab29043e99eaf62c31d0a8d33
出典データセット
uspto-grants-2013_06
特許番号
US08466182B2

反応ノート

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