Methanesulfonic Acid → 3-((3-(4-Chloro-2-hydroxyphenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide

HRID 453123노트

반응식

HRID 453123 반응식
C([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([CH2:21][O:22][C:23]2[C:24]([F:33])=[C:25]([C:29]([F:32])=[CH:30][CH:31]=2)[C:26]([NH2:28])=[O:27])[S:18][N:17]=1)C1C=CC=CC=1.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>ClCCl>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([C:16]2[N:20]=[C:19]([CH2:21][O:22][C:23]3[C:24]([F:33])=[C:25]([C:29]([F:32])=[CH:30][CH:31]=3)[C:26]([NH2:28])=[O:27])[S:18][N:17]=2)=[C:9]([OH:8])[CH:14]=1

참가 물질

5

반응물 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 595495353-((3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide

생성물 1

HCID 1358727333-((3-(4-Chloro-2-hydroxyphenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide수율 30.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-((3-(2-(benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluorobenzamide (0.05 g, 0.10 mmol) in dichloromethane (5 ml) was added methanesulfonic acid (0.50 ml, excess) at room temperature under nitrogen atmosphere and allowed to stir at same temperature for 90 min. After the completion of the reaction (TLC monitoring), the solution was cooled to 0° C. and basified with saturated NaHCO3 solution (aqueous) followed by extraction with EtOAc (3×25 ml). The combined organics was dried over anhydrous Na2SO4, filtered and concentrated. The residue was washed with ether to get the desired product (0.012 g, 30%).

후처리

  1. customAfter the completion of the reaction (TLC monitoring)
  2. extractionfollowed by extraction with EtOAc (3×25 ml)
  3. dry with materialThe combined organics was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe residue was washed with ether

출처 및 근거

ORD 기록
ord-b2a9751877294b129ea2d909eee6264a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492414B2

반응 노트

불러오는 중…