m-Chloroperbenzoic acid → HCID 23512655, compound

HRID 353910Notes

Reaction equation

HRID 353910 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([NH:7][C:8]([CH3:28])([CH3:27])[CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=[C:11]1[CH2:23][O:24][CH2:25][CH3:26])=[O:6])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:34]>C(Cl)Cl>[CH2:1]([O:3][CH2:4][C:5]([NH:7][C:8]([CH3:27])([CH3:28])[CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:15]([O-:34])=[CH:14][C:13]=2[N:12]=[C:11]1[CH2:23][O:24][CH2:25][CH3:26])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68829483HCID 68829483, compound

Product 1

HCID 23512655HCID 23512655, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-ethoxy-N-{2-[2-(ethoxymethy)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}acetamide (998 mg, 2.60 mmol) in 20 mL of CH2Cl2 was treated with 3-chloroperoxybenzoic acid (77%, 668 mg, 2.99 mmol). After stirring for 3 h, the reaction mixture was treated with 30 mL of additional CH2Cl2 and was washed with 1% Na2CO3 solution (2×50 mL), H2O and brine. The organic portion was then dried over Na2SO4 and concentrated to give 2-ethoxy-N-{2-[2-(ethoxymethy)-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}acetamide (910 mg) as a light brown oil.

Workup

  1. washwas washed with 1% Na2CO3 solution (2×50 mL), H2O and brine
  2. dry with materialThe organic portion was then dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-31f06fee3f534c95ac6a0aaf5e97d542
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

Loading…