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

HRID 453123ノート

反応式

HRID 453123 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b2a9751877294b129ea2d909eee6264a
出典データセット
uspto-grants-2013_07
特許番号
US08492414B2

反応ノート

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