Hydrochloric Acid → N-(3-Aminobenzyl)-3-nitrobenzenesulfonamide Hydrochloride

HRID 541807Notes

Reaction equation

HRID 541807 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:13][CH2:14][C:15]2[CH:16]=[C:17]([NH:21]C(=O)OC(C)(C)C)[CH:18]=[CH:19][CH:20]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[ClH:29]>O1CCOCC1>[ClH:29].[NH2:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[CH2:14][NH:13][S:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57962389HCID 57962389, compound

Product 1

HCID 66880208N-(3-Aminobenzyl)-3-nitrobenzenesulfonamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl [3-({[(3-nitrophenyl)sulfonyl]amino}methyl)phenyl]carbamate (1.00 g, 2.45 mmol) was mixed with 4 M of hydrogen chloride in 1,4-dioxane (10 mL) and stirred at rt for 2 h. After concentration, the crude off-white powder product (0.97 g) was used in the next step. (Molecular Formula (MF)=C13H13N3O4S; LCMS calculated for C13H13N3O4S (M+H)+: m/z=308.0. 1H NMR (400 MHz, CD3OD): δ 8.55 (t, J=2.0 Hz, 1H), 8.44 (ddd, J=8.4, 2.4, 1.2 Hz, 1H), 8.20 (ddd, J=7.6, 2.4, 1.2 Hz, 1H), 7.81 (t, J=8.0 Hz, 1H), 7.40 (m, 2H), 7.36 (dd, J=7.6, 1.2 Hz, 1H), 7.23 (ddd, J=8.0, 2.4, 1.2, 1H), 4.21 (s, 2H).

Workup

  1. concentrationAfter concentration

Sources & evidence

ORD record
ord-389fcaf4f8ce4ac2a377ed7bc9343300
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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