Benzenesulfonamide, N-[(4-methoxyphenyl)methyl]-2-nitro- → Benzenesulfonamide, N-[(4-methoxyphenyl)methyl]-2-nitro-

HRID 22879Notes

Reaction equation

HRID 22879 reaction equation
C(OC(=O)C1C=CC(CNS(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)=CC=1)(C)(C)C.[CH3:28][O:29][C:30]1[CH:49]=[CH:48][C:33]([CH2:34][NH:35][S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[N+:45]([O-:47])=[O:46])(=[O:38])=[O:37])=[CH:32][CH:31]=1>>[CH3:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:34][NH:35][S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[N+:45]([O-:47])=[O:46])(=[O:37])=[O:38])=[CH:48][CH:49]=1.[NH2:45][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[S:36]([NH:35][CH2:34][C:33]1[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:49][CH:48]=1)(=[O:37])=[O:38]

Participants

4

Reactant 2

HCID 796366Benzenesulfonamide, N-[(4-methoxyphenyl)methyl]-2-nitro-HCID 697944154-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

Product 2

HCID 796366Benzenesulfonamide, N-[(4-methoxyphenyl)methyl]-2-nitro-HCID 11339912-amino-N-(4-methoxy-benzyl)-benzenesulfonamide

Procedure

When in the procedure of Example 17, Step (2), 4-[(2-nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester was replaced with N-(4-methoxy-benzyl)-2-nitro-benzenesulfonamide, the title compound 2-amino-N-(4-methoxy-benzyl)-benzenesulfonamide was obtained as a thick oil. 1H-NMR (CDCl3); δ 7.71 (dd, 1H), 7.07 (d, 2H), 6.78 (m, 4H), 4.93 (bt, 1H), 4.82 (bs, 2H), 3.95 (d, 2H), and 3.75 (s, 3H). MS: M+−1=291.0 Da Step (3): Synthesis of 2-Amino-5-bromo-N-(4-methoxy-benzyl)-benzenesulfonamide

Sources & evidence

ORD record
ord-a1c0cd5e0a54433c8c51fba9e71b84e4
Source dataset
uspto-grants-2005_02
Patent number
US06849648B2

Reaction notes

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