3,4-Dimethoxybenzenesulfonyl chloride → 3,4-Dimethoxy-N-(1-methyl-3-phenyl-1,2,4-triazol-5-yl)benzenesulfonamide

HRID 655990ノート

反応式

HRID 655990 の反応式
[CH3:1][N:2]1[C:6]([NH2:7])=[N:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N: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.CC(O)=O.O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([S:24]([NH:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:5]=2)(=[O:25])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

参加物

6

反応物 2

HCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 125813071-methyl-3-phenyl-1H-1,2,4-triazol-5-amine

生成物 1

HCID 249945063,4-Dimethoxy-N-(1-methyl-3-phenyl-1,2,4-triazol-5-yl)benzenesulfonamide収率 19.1%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 1049Pyridine溶媒

実験手順

To a solution of 1-methyl-3-phenyl-1,2,4-triazol-5-amine (320 mg, 2 mmol) in 10 mL 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 salt was partitioned between EtOAc and water. The EtOAc phase was extracted alternately with 1M NaOH and H2O. The basic phase was made acid (pH˜3) with 1M HCl and extracted with EtOAc. The organic phase was evaporated in vacuo, toluene was added and was again evaporated in vacuo to give a white solid. The product was taken up in hot HOAc (16 mL), diluted with H2O (10 mL) and seeded to give 143 mg of white needles with mp 279-280° C. after drying in vacuo.

後処理

  1. customthe pyridine was removed in vacuo
  2. customThe salt was partitioned between EtOAc and water
  3. extractionThe EtOAc phase was extracted alternately with 1M NaOH and H2O
  4. extractionextracted with EtOAc
  5. customThe organic phase was evaporated in vacuo, toluene
  6. additionwas added
  7. customwas again evaporated in vacuo
  8. customto give a white solid

出典と根拠

ORDレコード
ord-e7266adc3ee24e3f8614e387290f5b73
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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