m-Chloroperbenzoic acid → HCID 67545303, compound

HRID 389059Notes

Reaction equation

HRID 389059 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([O:15][CH2:16][C:17]1[S:18][C:19]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=[CH:21][C:20]=2[N:29]=1)(=[O:14])[CH3:13]>C(Cl)(Cl)Cl>[C:12]([O:15][CH2:16][C:17]1[S:18][C:19]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N+:22]([O-:6])=[CH:21][C:20]=2[N:29]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22648274HCID 22648274, compound

Product 1

HCID 67545303HCID 67545303, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperoxybenzoic acid (mCPBA) (34.7 grams (g) of 77% purity, 155 millimoles (mmol)) was added over a period of 15 minutes to a solution of [1,3]thiazolo[4,5-c]quinolin-2-ylmethyl acetate (U.S. Pat. No. 6,110,929, Example 37 Parts A and B, 20.0 g, 77.4 mmol) in chloroform (500 milliliters (mL)), and the reaction was stirred for two hours at room temperature and subsequently washed with aqueous sodium carbonate (500 mL of 10% weight/weight (w/w)). The organic layer was dried over magnesium sulfate and filtered to provide a solution of (5-oxido[1,3]thiazolo[4,5-c]quinolin-2-yl)methyl acetate in chloroform.

Workup

  1. washsubsequently washed with aqueous sodium carbonate (500 mL of 10% weight/weight (w/w))
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-adb114b563904f76b85151f10754dc6c
Source dataset
uspto-grants-2013_02
Patent number
US08378102B2

Reaction notes

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