m-Chloroperbenzoic acid → HCID 54383742, compound

HRID 2412395Notes

Reaction equation

[CH:1](=[N:8][S:9][C:10]1[C:11]([Cl:16])=[N:12][CH:13]=[CH:14][N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-:18].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[CH:1](=[N:8][S:9]([C:10]1[C:11]([Cl:16])=[N:12][CH:13]=[CH:14][N:15]=1)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.25 grams (0.005 mole) of N-benzylidene-2-chloropyrazine-3-sulfenamide in 25 milliliters of chloroform was added to a rapidly stirring mixture of 0.69 gram (0.25 millimole) of sodium bicarbonate and the resulting mixture cooled to 0° C. To the cooled solution, a solution of gram (5.5 millimole) of m-chloroperbenzoic acid in 25 milliliter of chloroform was added dropwise over a 15 minute period. After completion of the addition, stirring was continued for 15 hours. At the end of this period, chloroform layer was separated from the aqueous layer, dried over anhydrous potassium carbonate, and subjected to reduced pressure to remove the solvent and to recover as residue an oil which solidified on standing. The latter was purified by crystallization from ethanol to obtain the desired N-benzylidene-2-chloropyrazine-3-sulfinamide product, m.p. 113°-114° C. Elemental analyses were as follows:

Workup

additionAfter completion of the addition
stirringstirring
customAt the end of this period, chloroform layer was separated from the aqueous layer
dry with materialdried over anhydrous potassium carbonate
customto remove the solvent
customto recover as residue an oil which
customThe latter was purified by crystallization from ethanol

Sources & evidence

ORD record: ord-94b19d0803a046308476b72f7902bd0c
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04492700

Reaction notes

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