Methanesulfonic Acid → 2,6-Difluoro-3-[3-(4-hydroxyphenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-benzamide

HRID 453109Notes

Reaction equation

HRID 453109 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[C:18]([CH2:20][O:21][C:22]3[C:23]([F:32])=[C:24]([C:28]([F:31])=[CH:29][CH:30]=3)[C:25]([NH2:27])=[O:26])[S:17][N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CS(O)(=O)=O>C(Cl)Cl>[F:32][C:23]1[C:22]([O:21][CH2:20][C:18]2[S:17][N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[N:19]=2)=[CH:30][CH:29]=[C:28]([F:31])[C:24]=1[C:25]([NH2:27])=[O:26]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 595495343-[3-(4-Benzyloxyphenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-2,6-difluorobenzamide

Product 1

HCID 1358727302,6-Difluoro-3-[3-(4-hydroxyphenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-benzamideYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-(4-benzyloxy-phenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-2,6-difluorobenzamide (0.020 g, 0.04 mmol) in DCM (5 ml) was added methanesulfonic acid (0.15 g, 1.50 mmol) drop wise. The resulting reaction mixture was stirred at room temperature for 1 h. After the completion of the reaction (TLC monitoring), the reaction mass was cooled to 0° C., quenched it with 5 ml of water and concentrated under vacuum. Added 25 ml water and extracted with ethyl acetate (3×20 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified by ether and DCM washes to get the desired product (0.004 g, 25%).

Workup

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. temperaturethe reaction mass was cooled to 0° C.
  4. customquenched it with 5 ml of water
  5. concentrationconcentrated under vacuum
  6. additionAdded 25 ml water
  7. extractionextracted with ethyl acetate (3×20 ml)
  8. dry with materialThe combined organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe crude residue was purified by ether and DCM

Sources & evidence

ORD record
ord-2bed009385014346916330ca86104509
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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