1-Methyl-3-phenyl-1H-pyrazol-5-amine → 3,4-Dimethoxy-N-[1-methyl-3-phenyl-pyrazol-5-yl]benzenesulfonamide

HRID 655989

반응식

HRID 655989 반응식
[CH3:1][N:2]1[C:6]([NH2:7])=[CH: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>[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)[CH:5]=2)(=[O:25])=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

참가 물질

4

반응물 2

HCID 5177791-Methyl-3-phenyl-1H-pyrazol-5-amineHCID 27341833,4-Dimethoxybenzenesulfonyl chloride

생성물 1

HCID 28152693,4-Dimethoxy-N-[1-methyl-3-phenyl-pyrazol-5-yl]benzenesulfonamide수율 93.7%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 1-methyl-3-phenyl-pyrazol-5-amine (346 mg, 2 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 22 h, the pyridine was removed in vacuo and flashed off with toluene. The crude base soluble material (1M NaOH) weighed 1.1 g. The crude product was taken up in EtOAc and extracted with 1M NaOH and H2O alternately. The basic aqueous phase was made acidic with 1M HCl, extracted with EtOAc, washed with water, dried and evaporated in vacuo to give a cream colored solid (0.70 g) which was taken up in 5 mL of hot EtOH, diluted with 5 mL of H2O and seeded to give 473 mg of a solid with mp 163-165° C. after drying in vacuo.

후처리

  1. customthe pyridine was removed in vacuo
  2. extractionextracted with 1M NaOH and H2O alternately
  3. extractionextracted with EtOAc
  4. washwashed with water
  5. customdried
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-5b870dbb0b52402ebfd29b15263149e7
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071631B2

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