Acetic Acid → HCID 86743483, compound

HRID 2107944Notes

Reaction equation

HRID 2107944 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10](=[O:27])[C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([NH:18][C:19](=[O:21])[CH3:20])=[CH:13][C:12]=1[O:22][CH2:23][CH:24]1[CH2:26][CH2:25]1)[CH2:2]2.C(O)(=[O:30])C>OO>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([NH+:9]([O-:30])[C:10](=[O:27])[C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([NH:18][C:19](=[O:21])[CH3:20])=[CH:13][C:12]=1[O:22][CH2:23][CH:24]1[CH2:25][CH2:26]1)[CH2:2]2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 23044933HCID 23044933, compound

Product 1

HCID 86743483HCID 86743483, compound

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-(1-azabicyclo[2.2.2]oct-3-yl)-2-cyclopropylmethoxy-4-acetamido-5-chlorobenzamide (2.6 g; 0.007 moles) in acetic acid (20 ml), 30% hydrogen peroxide (1.8 ml) was added and the resulting solution was stirred at 80° C. for 15 hours. The solvent was removed in vacuo, the residue was treated with water, alcalinized with sodium hydroxide aqueous solution, saturated with sodium chloride and extracted with methylene chloride. The organic solution was dried (Na2SO4), the solvent removed in vacuo and the residual yellow solid treated with diethyl ether and collected. After washing with acetonitrile and diethyl ether, N-(1-azabicyclo[2.2.2]oct-3-yl)-2-cyclopropylmethoxy-4-acetamido-5-chlorobenzamide N-oxide was obtained as a white solid, which was dried at 50° C. to give 1.4 g; m.p. 234°-236° C. (d).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was treated with water
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. customthe solvent removed in vacuo
  6. additionthe residual yellow solid treated with diethyl ether
  7. customcollected
  8. washAfter washing with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-b4b8468fc9604fde8da745f3832ebaed
Source dataset
uspto-grants-1990_06
Patent number
US04937236

Reaction notes

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