Methanol → 3-Amino-2-benzyl-5-[(butylamino)methyl]benzene-1-sulfonamide

HRID 1390056Notes

Reaction equation

HRID 1390056 reaction equation
Br.[NH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6]Br.[CH2:22]([NH2:26])[CH2:23][CH2:24][CH3:25].CO>O>[NH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([S:18](=[O:21])(=[O:20])[NH2:19])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][NH:26][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 887MethanolHCID 8007ButylamineHCID 202945373-Amino-4-benzyl-5-sulfamylbenzylbromide hydrobromide

Product 1

HCID 202945453-Amino-2-benzyl-5-[(butylamino)methyl]benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-amino-4-benzyl-5-sulfamylbenzyl bromide hydrobromide (1.1 g; prepared as described in Example 61), n-butylamine (5.0 ml) and methanol (10 ml) is stirred at 22°-25° C. for 24 hours. The resulting solution is then diluted with water (20 ml) to precipitate crude (3-amino-4-benzyl-5-sulfamylbenzyl)-n-butylamine. After filtration and recrystallization from aqueous ethanol it is obtained with a melting point of 141°-143° C.

Workup

  1. customto precipitate crude (3-amino-4-benzyl-5-sulfamylbenzyl)-n-butylamine
  2. filtrationAfter filtration and recrystallization from aqueous ethanol it
  3. customis obtained with a melting point of 141°-143° C.

Sources & evidence

ORD record
ord-989c2c1489044c9aa94337bc5ba4b175
Source dataset
uspto-grants-1981_01
Patent number
US04247550

Reaction notes

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