m-Chloroperbenzoic acid → 4-(7-chloro-2-(methylsulfinyl)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide

HRID 2370563Notes

Reaction equation

HRID 2370563 reaction equation
[Cl:1][C:2]1[C:10]2[S:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH3:23])=[O:21])[CH:15]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1>C(Cl)Cl>[Cl:1][C:2]1[C:10]2[S:9][C:8]([S:11]([CH3:12])=[O:32])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:20]([NH:22][CH3:23])=[O:21])[CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 577256274-(7-chloro-2-(methylthio)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide

Product 1

HCID 577257514-(7-chloro-2-(methylsulfinyl)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 4-(7-chloro-2-(methylthio)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide (64 mg, 0.175 mmol, 1.0 eq) in 5 mL of DCM was added MCPBA (33 mg, 0.192 mmol, 1.1 eq) at 0° C. and reaction stirred for 30-45 min. Thereafter, it was quenched with water (10 mL) and aqueous phase extracted with ethyl acetate (25 mL×5), combined organic layers dried over sodium sulfate, filtered and condensed under reduced pressure to yield crude product which was sufficiently pure and was carried to next step without further purification. LC/MS (m/z) [382.0] (MH+)

Workup

  1. customreaction
  2. customThereafter, it was quenched with water (10 mL) and aqueous phase
  3. extractionextracted with ethyl acetate (25 mL×5)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customcondensed under reduced pressure
  7. customto yield crude product which
  8. customwas carried to next step without further purification

Sources & evidence

ORD record
ord-2801745c0ca448119ef56e7a6eff8af3
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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