Acetic Acid → 3-Amino-4-benzyl-5-sulfamylbenzylbromide hydrobromide

HRID 1390054Notes

Reaction equation

HRID 1390054 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([S:17](=[O:20])(=[O:19])[NH2:18])[C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5]O.C(O)(=O)C.[BrH:25]>C(OCC)C>[BrH:25].[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([S:17](=[O:20])(=[O:19])[NH2:18])[C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][Br:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 536869293-Amino-2-benzyl-5-(hydroxymethyl)benzene-1-sulfonamide

Product 1

HCID 202945373-Amino-4-benzyl-5-sulfamylbenzylbromide hydrobromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Amino-4-benzyl-5-sulfamylbenzyl alcohol (12.5 g; prepared as described in Example 4) is while stirring added in portions to acetic acid saturated with dry hydrogen bromide (60 ml), and the mixture is stirred for 24 hours. The resulting solution is diluted with diethyl ether (150 ml) and cooled to precipitate 3-amino-4-benzyl-5-sulfamylbenzyl bromide hydrobromide as a hygroscopic material with a melting point of 195°-198° C.

Workup

  1. stirringthe mixture is stirred for 24 hours
  2. temperaturecooled
  3. customto precipitate 3-amino-4-benzyl-5-sulfamylbenzyl bromide hydrobromide as a hygroscopic material with a melting point of 195°-198° C.

Sources & evidence

ORD record
ord-be722eee992243dd98d238ae479cf8cb
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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