m-Chloroperbenzoic acid → UK-333747

HRID 842662Notes

Reaction equation

HRID 842662 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Cl:12][C:13]1[C:14]([N:26]2[C:30]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)=[N:29][N:28]=[C:27]2[CH2:37][O:38][CH3:39])=[C:15]2[C:20](=[CH:21][C:22]=1[Cl:23])[NH:19][C:18](=[O:24])[C:17](=[O:25])[NH:16]2>CC(C)=O>[Cl:12][C:13]1[C:14]([N:26]2[C:30]([C:31]3[CH:32]=[N+:33]([O-:6])[CH:34]=[CH:35][CH:36]=3)=[N:29][N:28]=[C:27]2[CH2:37][O:38][CH3:39])=[C:15]2[C:20](=[CH:21][C:22]=1[Cl:23])[NH:19][C:18](=[O:24])[C:17](=[O:25])[NH:16]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 9802164HCID 9802164, compound

Product 1

HCID 9867605UK-333747Yield 17%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 3-chloroperoxybenzoic acid (0.85 g, 4.93 mmol) in acetone (20 ml) was added in one portion to a suspension of (−)-6,7-dichloro-5-[3-methoxymethyl-5-(3-pyridyl)-4H-1,2,4-triazol-4-yl]-2,3(1H,4H)-quinoxalinedione (see Example 111) (1.0 g, 2.24 mmol) in acetone (40 ml) which caused all the solid to dissolve. The reaction was stirred at room temperature for 40 minutes after which time a white solid began to form. The reaction mixture was allowed to stir at room temperature for 3 days. The white solid was collected by filtration and purified by flash chromatography on silica gel using dichloromethane:methanol:glacial acetic acid (90:10:1, by volume) as eluent, to give after combination and concentration of the appropriate fractions, the title compound (0.16 g, 17%) as a white solid, m.p. >310° C.

Workup

  1. dissolutionto dissolve
  2. customto form
  3. stirringto stir at room temperature for 3 days
  4. filtrationThe white solid was collected by filtration
  5. custompurified by flash chromatography on silica gel
  6. custommethanol:glacial acetic acid (90:10:1, by volume) as eluent, to give after combination and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-892870667f4842d4ac1726a116b620c0
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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