N,N-Dimethylethylenediamine → HCID 13785476, compound
Reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=1[C:7]([O:9]C)=[O:8])(=[O:4])=[O:3].[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH2:22]>C1COCC1>[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH:22][S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=1[C:7]([OH:9])=[O:8])(=[O:4])=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methyl 2-chlorosulfonyl-6-nitrobenzoate (500 mg, 1.79 mmol) and 2-dimethylaminoethylamine (316 mg, 3.58 mmol) in THF (35 ml) was stirred in an ice bath for 1 hour then at 20°-25° for 18 hours. After removing THF under reduced pressure, the residue was partitioned between saturated Na2CO3 solution and EtOAc. The organic extract was washed (saturated NaCl solution), dried (Na2SO4), filtered and concentrated under reduced pressure. Chromatography over silica gel (elution with 5% MeOH-95% CHCl3) gave an oil which when triturated with EtOAc afforded 2-[N-(2-dimethylaminoethyl)aminosulfonyl]-6-nitrobenzoic acid (90 mg, 16%), m.p. 193° decomposed with effervescence.