m-Chloroperbenzoic acid → 2-Methanesulfinylmethyl-3-methoxy-benzoic acid n'-tert-butyl-n'-(3,5-dimethyl-benzoyl)-hydrazide

HRID 39636Notes

Reaction equation

HRID 39636 reaction equation
[C:1]([N:5]([C:20](=[O:29])[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=1)[NH:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[CH2:16][S:17][CH3:18])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:38])C=1>C(Cl)Cl>[C:1]([N:5]([C:20](=[O:29])[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=1)[NH:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[CH2:16][S:17]([CH3:18])=[O:38])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 598385893-Methoxy-2-methylsulfanylmethyl-benzoic acid n'-tert-butyl-n'-(3,5-dimethyl-benzoyl)-hydrazide

Product 1

HCID 598386012-Methanesulfinylmethyl-3-methoxy-benzoic acid n'-tert-butyl-n'-(3,5-dimethyl-benzoyl)-hydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methoxy-2-methylsulfanylmethyl-benzoic acid N′-tert-butyl-N′-(3,5-dimethyl-benzoyl)-hydrazide in CH2Cl2 was stirred at room temperature with 1.0 eq of m-chloroperbenzoic acid. The reaction was complete within 5 min as indicated by TLC. The reaction mixture was washed with saturated NaHCO3 and the organic layer was stripped under vacuum. The residue was mixed with 1-2 mL of 1:1 ether:hexane and the solution was removed with a pipette, leaving the product which was then dried under vacuum.

Workup

  1. washThe reaction mixture was washed with saturated NaHCO3
  2. additionThe residue was mixed with 1-2 mL of 1:1 ether
  3. customhexane and the solution was removed with a pipette
  4. customleaving the product which
  5. customwas then dried under vacuum

Sources & evidence

ORD record
ord-1fe64466950c4ac4a76520782f838178
Source dataset
uspto-grants-2013_09
Patent number
US08524948B2

Reaction notes

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