m-Chloroperbenzoic acid → HCID 15676629, compound

HRID 483613Notes

Reaction equation

HRID 483613 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH:12]([C:15]1([CH3:39])[C:19](=[O:20])[NH:18][C:17]([C:21]2[N:30]=[CH:29][C:28]([CH2:31][S:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])=[N:16]1)([CH3:14])[CH3:13].C(=O)(O)[O-].[Na+]>C(Cl)Cl.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[CH:12]([C:15]1([CH3:39])[C:19](=[O:20])[NH:18][C:17]([C:21]2[N:30]=[CH:29][C:28]([CH2:31][S:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:6])=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])=[N:16]1)([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 15676628HCID 15676628, compound

Product 1

HCID 15676629HCID 15676629, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 656671Sodium PyrosulfiteSolvent

Conditions

Temperature
-78 °C

Procedure

3-Chloroperoxybenzoic acid (20 mL, 0.00252 mol) is added dropwise to a -78° C. solution of 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-[(phenylthio)methyl]nicotinic acid, methyl ester (1.0 g, 0.00252 mol) and sodium bicarbonate (0.2 g, 0.00238 mol) in methylene chloride. The reaction mixture is stirred at -78° C. for 30 minutes and then at room temperature for 24 hours. The reaction mixture is diluted with 5% sodium metabisulfite solution. The methylene chloride layer is separated, washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield a yellow oil. The oil is chromatographed using silica gel and hexanes/ethyl acetate (1:1) to (1:2) to (1:9) and finally 100% ethyl acetate as eluant to give the title compound as a yellow solid (0.97 g, 90%), mp 132°-136° C., identified by IR and NMR spectral analyses.

Workup

  1. waitat room temperature for 24 hours
  2. customThe methylene chloride layer is separated
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto yield a yellow oil
  7. customThe oil is chromatographed

Sources & evidence

ORD record
ord-de773824f7ff49a78a1a15b8553f33c0
Source dataset
uspto-grants-1993_07
Patent number
US05225564

Reaction notes

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