(3-n-Butylamino-4-phenoxy-5-sulfamylbenzyl)benzylamine → 5-(Aminomethyl)-3-(butylamino)-2-phenoxybenzene-1-sulfonamide
Reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:18]=[C:19]([S:28](=[O:31])(=[O:30])[NH2:29])[C:20]=1[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:9][NH:10]CC1C=CC=CC=1)[CH2:2][CH2:3][CH3:4]>COCCO.[Pd]>[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:18]=[C:19]([S:28](=[O:31])(=[O:30])[NH2:29])[C:20]=1[O:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:9][NH2:10])[CH2:2][CH2:3][CH3:4]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (3-n-butylamino-4-phenoxy-5-sulfamylbenzyl)benzylamine (8.8 g; prepared as described in Example 136) in 2-methoxyethanol (90 ml), palladium (10%) on carbon (4.0 g) is added and the mixture is hydrogenated. After about 5 hours the theoretical amount of hydrogen has been absorbed, and the mixture is heated on a steam-bath and filtered to remove the catalyst. The filtrate is evaporated in vacuo and the residue triturated with water to yield crude 3-n-butylamino-4-phenoxy-5-sulfamylbenzylamine. The crude amine is dissolved in formic acid (50 ml), whereafter the solution is evaporated in vacuo. The residue is recrystallized from a mixture of ethanol and 2-methoxyethanol to yield, after filtration and drying, 3-n-butylamino-4-phenoxy-5-sulfamylbenzylamine formate hemihydrate with a melting point of 224°-226° C.
Workup
- customAfter about 5 hours the theoretical amount of hydrogen has been absorbed
- temperaturethe mixture is heated on a steam-bath
- filtrationfiltered
- customto remove the catalyst
- customThe filtrate is evaporated in vacuo
- customthe residue triturated with water
Sources & evidence
- ORD record
- ord-afb865bd3f454ff49ebbe13db5bb3af5
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04247550
Reaction notes
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