Bromine → N-phenyl-2-(methylsulfinyl)benzamide

HRID 1379909Notes

Reaction equation

HRID 1379909 reaction equation
[C:1]1([NH:7][C:8](=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-:19].[K+].BrBr>C1(C)C=CC=CC=1>[C:1]1([NH:7][C:8](=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH3:16])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 152460HCID 152460, compoundHCID 516893Potassium Bicarbonate

Product 1

HCID 11832126N-phenyl-2-(methylsulfinyl)benzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 1000 ml four-necked flask equipped with a stirrer, a thermometer, and a condenser, 48.6 g (0.2 mol) of N-phenyl-2-(methylthio)benzamide obtained in Example 1, 300 g of toluene, and 200 g of a 10% by weight aqueous solution of potassium bicarbonate are placed. To the above mixture in the flask, 32.0 g (0.2 mol) of bromine is added dropwise while stirring at a temperature of from 10° to 15° C. to be allowed to react with each other for about 10 minutes. After completion of the reaction, the produced white crystals are filtered and then recrystallized from a mixture of water and ethanol (1:9) to give 48.7 g of N-phenyl-2-(methylsulfinyl)benzamide (melting point: 194° to 195° C.). The yield of the product against N-phenyl-2-(methylthio)benzamide is 94%.

Workup

  1. customTo a 1000 ml four-necked flask equipped with a stirrer
  2. customto react with each other for about 10 minutes
  3. customAfter completion of the reaction
  4. filtrationthe produced white crystals are filtered
  5. customrecrystallized from a mixture of water and ethanol (1:9)

Sources & evidence

ORD record
ord-5b6480808eeb4684a63b49f6b65059f4
Source dataset
uspto-grants-1997_09
Patent number
US05672751

Reaction notes

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