m-Chloroperbenzoic acid → HCID 68516539, compound

HRID 1948302Notes

Reaction equation

HRID 1948302 reaction equation
Cl[C:2]1C=CC=C(C(OO)=O)C=1.[CH3:12][C:13]([NH:21][C:22]([C:24]1[N:25]=[C:26](SC)[S:27][C:28]=1[C:29]([O:31][CH3:32])=[O:30])=[O:23])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14].[S:35](=[O:38])(O)[O-:36].[Na+]>C(Cl)Cl>[CH3:14][C:13]([NH:21][C:22]([C:24]1[N:25]=[C:26]([S:35]([CH3:2])(=[O:38])=[O:36])[S:27][C:28]=1[C:29]([O:31][CH3:32])=[O:30])=[O:23])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:12]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 59406865HCID 59406865, compound2×

Product 1

HCID 68516539HCID 68516539, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (0.89 g) was added to a solution of methyl 4-{[(1-methyl-1-phenylethyl)amino]carbonyl}-2-(methylthio)-1,3-thiazole-5-carboxylate (Intermediate 15; 0.63 g) in DCM (25 ml). After stirring overnight the reaction was complete. Aqueous sodium bisulfite was added to quench any unreacted peroxides and the solution was washed with sat. NaHCO3. The organic portion was dried with MgSO4 and concentrated to a yellow solid (0.6 g). NMR: 1.63-1.68 (m, 6H), 3.58 (s, 3H), 3.89 (s, 3H), 7.23 (d, J=7.16 Hz, 1H), 7.34 (t, J=7.63 Hz, 2H), 7.47 (d, J=7.54 Hz, 2H), 8.91 (s, 1H).

Workup

  1. customto quench any unreacted peroxides
  2. washthe solution was washed with sat. NaHCO3
  3. dry with materialThe organic portion was dried with MgSO4
  4. concentrationconcentrated to a yellow solid (0.6 g)

Sources & evidence

ORD record
ord-c5596f1e7e4e479c8de9cf90475b8a42
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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