m-Chloroperbenzoic acid → HCID 20344104, compound

HRID 2049638Notes

Reaction equation

HRID 2049638 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([S:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:7][CH:8]=2)[CH:3]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([S:15]([CH2:16][CH:17]([CH3:19])[CH3:18])=[O:28])=[CH:7][CH:8]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20344103HCID 20344103, compound

Product 1

HCID 20344104HCID 20344104, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 0.1 mol of 2-amino-7-isobutylthio-3-nitronaphthalene, prepared in Example 5, stirring in 200 ml of chloroform at 4°-6° (ice bath), is added 0.1 mol of m-chloroperbenzoic acid in 160 ml of chloroform over 3 hours. Consumption of starting material is confirmed by TLC (silica gel, ether). The reaction mixture is washed 3 times with saturated NaHCO3 solution, dried (Na2SO4), and filtered. The filtrate is evaporated to dryness under vacuum and the residue recrystallized from ethanol (absolute) to yield the title compound.

Workup

  1. customConsumption of starting material
  2. washThe reaction mixture is washed 3 times with saturated NaHCO3 solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate is evaporated to dryness under vacuum
  6. customthe residue recrystallized from ethanol (absolute)

Sources & evidence

ORD record
ord-21ab38f667ec44b99a9aa383b97deb29
Source dataset
uspto-grants-1980_04
Patent number
US04198422

Reaction notes

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