4-Sulfamoylbenzaldehyde → 4-(2-Cyanoethyl)benzene-1-sulfonamide

HRID 973755Notes

Reaction equation

HRID 973755 reaction equation
[NH2:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:13]([CH2:15]P(=O)(OCC)OCC)#[N:14].[H-].[Na+]>O1CCCC1>[C:13]([CH2:15][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([S:2]([NH2:1])(=[O:4])=[O:3])=[CH:6][CH:7]=1)#[N:14]

Participants

4

Reactant 2

HCID 1510884-SulfamoylbenzaldehydeHCID 86740749Diethyl cyanomethylphosphonate sodium hydride

Product 1

HCID 198091824-(2-Cyanoethyl)benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For the preparation of the amine starting material of Example 24, p-aminosulfonylbenzaldehyde was reacted with diethyl cyanomethylphosphonate/sodium hydride in tetrahydrofuran to give 1-cyano-2-(4-aminosulfonylphenyl)-ethane which was hydrogenated in methanol with Raney-cobalt as the catalyst to give 3-(4-aminosulfonylphenyl)-propylamine.

Sources & evidence

ORD record
ord-814dc3e2e5d1461c9a9a59f4a0a9956c
Source dataset
uspto-grants-1991_11
Patent number
US05064863

Reaction notes

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