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

HRID 453123Notes

Reaction equation

HRID 453123 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b2a9751877294b129ea2d909eee6264a
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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