Hydrogen Peroxide → HCID 178483450, compound

HRID 25617

Reaction equation

HRID 25617 reaction equation
OO.NC(N)=[O:5].C1(=O)OC(=O)C2=CC=CC=C12.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:44])[N:27]([C@H:29]2[CH2:34][CH2:33][C@H:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]([CH3:43])[CH3:42])[CH2:31][CH2:30]2)[CH3:28])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26](=[O:44])[N+:27]([O-:5])([C@H:29]2[CH2:34][CH2:33][C@H:32]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]([CH3:42])[CH3:43])[CH2:31][CH2:30]2)[CH3:28])=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 1176UreaHCID 6811Phthalic AnhydrideHCID 11430Potassium CarbonateHCID 178483449HCID 178483449, compound

Product 1

HCID 178483450HCID 178483450, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 1.39 g (4.4 mmol, 2.2 eq) Hydrogen peroxide.Urea adduct in CH2Cl2, 338.5 mg (2.2 mmol, 1.1 eq) phthalic anhydride were added and stirred for 15 min at RT. 800 mg (2.01 mmol) trans-[4-(5-Dimethylamino-pentyloxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester in CH2Cl2 was added and the mixture was stirred at RT for 2 h. 5% aqueous K2CO3 solution was added and the inorganic phase was extracted with CH2Cl2. The organic phases were washed with water and brine and dried over MgSO4. Column chromatography yielded 525 mg (63%) trans-[4-(5-Dimethylamino-pentyloxy)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester N-oxide as colourless oil, MS: 413 (MH+, 1Cl).

Workup

  1. stirringthe mixture was stirred at RT for 2 h
  2. extractionthe inorganic phase was extracted with CH2Cl2
  3. washThe organic phases were washed with water and brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-3dc8f3bc5c254208a25af1057fbd914b
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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