2-Methoxyaniline → N-(2-methoxyphenyl)4-(4-methyl-1-piperazinyl)-3-nitrobenzenesulfonamide

HRID 230540Notes

Reaction equation

HRID 230540 reaction equation
ClC1C=CC(S(Cl)(=O)=O)=CC=1[N+]([O-])=O.COC1C=CC=CC=1N.Cl[C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:41][CH3:42])(=[O:33])=[O:32])=[CH:27][C:26]=1[N+:43]([O-:45])=[O:44].[CH3:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1>C(Cl)Cl.N1C=CC=CC=1>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[NH:34][S:31]([C:28]1[CH:29]=[CH:30][C:25]([N:50]2[CH2:51][CH2:52][N:47]([CH3:46])[CH2:48][CH2:49]2)=[C:26]([N+:43]([O-:45])=[O:44])[CH:27]=1)(=[O:33])=[O:32]

Participants

7

Reactant 4

HCID 70002-MethoxyanilineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 531671-MethylpiperazineHCID 28876834-chloro-N-(2-methoxyphenyl)-3-nitrobenzenesulfonamide

Product 1

HCID 22272549N-(2-methoxyphenyl)4-(4-methyl-1-piperazinyl)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

The compound was prepared from 4-chloro-3-nitrobenzenesulfonylchloride (1 g, 3.9 mmol), 2-methoxyaniline (0.53 mL, 4.7 mmol) and pyridine (1.6 mL) in CH2Cl2 (2 mL). 4-Chloro-N-(2-methoxyphenyl)-3-nitrobenzenesulfonamide (0.345 mg) was reacted with N-methylpiperazine (0.144 mL) to afford N-(2-methoxyphenyl)-4-(4-methyl-1-piperazinyl)-3-nitrobenzenesulfonamide which was treated with Raney-Ni and hydrazine monohydrate. The final product was isolated as its HCl salt 1H NMR (DMSO-d6) δ 7.185 (dd, 1H), 7.08 (dt, 1H), 6.975 (d, 1H), 6.91-6.94 (m, 2H); 6.84 (dt, 1H), 3.56 (s, 3H), 3.42-3.47 (m, 2H), 3.22-3.24 (m, 2H), 2.95 (bt, 2H), 2.79 (bs, 3H); MS (posESI) m/z=376.2 (M+H+).

Sources & evidence

ORD record
ord-679f2da9fb2340dfa968b7e0ae2164cf
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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