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

HRID 1988474Notes

Reaction equation

HRID 1988474 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-154e143726cd41bdbe20cbd446021c2e
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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