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

HRID 1390053Notes

Reaction equation

HRID 1390053 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-cb6f2699e75d4da4bf08e2393a3b34ac
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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