m-Chloroperbenzoic acid → HCID 13635628, compound

HRID 509188Notes

Reaction equation

HRID 509188 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6](/[CH:7]=[N:8]/[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1>ClCCl>[CH:9]([N:8]1[CH:7]([C:6]2[CH:22]=[CH:23][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:32]1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178491052HCID 178491052, compound

Product 1

HCID 13635628HCID 13635628, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-N-(4-methoxybenzylidene)-1,1-diphenylmethanamine 39 (3.62 g, 12.0 mmol) was dissolved in dichloromethane (130 mL) at 0° C., followed by the portionwise addition of mCPBA (2.96 g, 13.2 mmol). The resulting solution was warmed to room temperature, and stirred for 16 h prior to being transferred to a separatory funnel, and being washed 3 times with 50 mL of saturated sodium bicarbonate solution. The organic layer was then dried with anhydrous sodium sulfate, filtered, and concentrated to afford 40 as a light yellow oil (3.52 g, 92%). LRMS (ESI): (calc.) 317.4 (found) 318.2 (MH)+.

Workup

  1. customto being transferred to a separatory funnel
  2. washbeing washed 3 times with 50 mL of saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was then dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d96c98be7f44444f88747d3f5644b51f
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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