Acetic Acid → 2-Benzyl-5-(bromomethyl)-3-(methylsulfanyl)benzene-1-sulfonamide

HRID 2082875Notes

Reaction equation

HRID 2082875 reaction equation
[CH2:1]([C:8]1[C:15]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:14][C:11]([CH2:12]O)=[CH:10][C:9]=1[S:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BrH:26]>O>[CH2:1]([C:8]1[C:15]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:14][C:11]([CH2:12][Br:26])=[CH:10][C:9]=1[S:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 20360840HCID 20360840, compound

Product 1

HCID 202945462-Benzyl-5-(bromomethyl)-3-(methylsulfanyl)benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Benzyl-3-methylthio-5-sulfamylbenzyl alcohol (10 g; prepared as described in Example 1) is while stirring added in portions to acetic acid saturated with dry hydrogen bromide (50 ml), and the mixture is stirred for 24 hours. The resulting solution is diluted with water (100 ml) and cooled to precipitate crude 4-benzyl-3-methylthio-5-sulfamylbenzyl bromide. After recrystallization from methanol it is obtained with a melting point of 149°-150° C.

Workup

  1. stirringthe mixture is stirred for 24 hours
  2. temperaturecooled
  3. customto precipitate crude 4-benzyl-3-methylthio-5-sulfamylbenzyl bromide
  4. customAfter recrystallization from methanol it
  5. customis obtained with a melting point of 149°-150° C.

Sources & evidence

ORD record
ord-ef3cca4b265c4bd985f8e350a76d95c7
Source dataset
uspto-grants-1978_04
Patent number
US04082851

Reaction notes

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