1,2,4-Thiadiazol-5-amine, 3-phenyl- → 3,4-Dimethoxy-n-[3-(phenyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide

HRID 655984ノート

反応式

HRID 655984 の反応式
[C:1]1([C:7]2[N:11]=[C:10]([NH2:12])[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23](Cl)(=[O:25])=[O:24])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>N1C=CC=CC=1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([S:23]([NH:12][C:10]2[S:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:11]=2)(=[O:24])=[O:25])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

参加物

4

反応物 2

HCID 285611,2,4-Thiadiazol-5-amine, 3-phenyl-HCID 27341833,4-Dimethoxybenzenesulfonyl chloride

生成物 1

HCID 249938883,4-Dimethoxy-n-[3-(phenyl)-1,2,4-thiadiazol-5-yl]benzenesulfonamide収率 14.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

3-Phenyl-1,2,4-thiadiazol-5-amine (326 mg, 1.84 mmol) was dissolved in dry pyridine (10 mL). Then 3,4-dimethoxybenzenesulfonyl chloride (529 mg, 2.23 mmol) was added. The solution was stirred at room temperature under Argon. After 46 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. After drying over Na2SO4, the solvent was removed in vacuo to give a solid (100 mg) which was crystallized from EtOAc. Yield was 29.3 mg; mp 170-171° 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. dry with materialAfter drying over Na2SO4
  6. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-c5de9be79a6a46839521373a51af5fe9
出典データセット
uspto-grants-2011_12
特許番号
US08071631B2

反応ノート

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