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

HRID 655984노트

반응식

HRID 655984 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c5de9be79a6a46839521373a51af5fe9
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071631B2

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