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

HRID 655990노트

반응식

HRID 655990 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e7266adc3ee24e3f8614e387290f5b73
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071631B2

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