Ethylenediamine → N-(2-Aminoethyl)-2-nitrobenzenesulfonamide

HRID 1072076Notes

Reaction equation

HRID 1072076 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14](Cl)(=[O:16])=[O:15])([O-:7])=[O:6]>C(Cl)Cl>[NH2:3][CH2:2][CH2:1][NH:4][S:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N+:5]([O-:7])=[O:6])(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 11471557N-(2-Aminoethyl)-2-nitrobenzenesulfonamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethylene diamine (268 mL, 20 equiv) in DCM (400 mL) was added to an ice-cooled solution of o-nitrobenzene sulfonyl chloride (44.4 gm, 0.2 mole) in DCM (200 mL) over 1 hr. Concentration on the rotary evaporator left an oil which was partitioned between DCM and sat. aq. Na2CO3 solution. The aqueous phase was backextracted with DCM and the combined organic phases were dried (Na2SO4). Removal of the solvents followed by silica gel chromatography (step gradient elution with DCM containing 0, 5, 10, 20, 30% MeOH) afforded the title compound as an oil (37.2 gm, 76%). 1H NMR (CDCl3+D2O) δ 2.82 (t, 2H, J=5.1 Hz), 3.10 (t, 2H, J=5.1 Hz), 7.73 (m, 2H), 7.83 (m, 1H), 8.11 (m, 1H); MS: 246 (M+H)+; HPLC Ret Time: 0.39 min (YMC Xterra 3.0×50 mm S7 C18 column, 3 min gradient, 4 mL/min).

Workup

  1. concentrationConcentration
  2. customon the rotary evaporator
  3. waitleft an oil which
  4. customwas partitioned between DCM and sat. aq. Na2CO3 solution
  5. dry with materialthe combined organic phases were dried (Na2SO4)
  6. customRemoval of the solvents
  7. washfollowed by silica gel chromatography (step gradient elution with DCM containing 0, 5, 10, 20, 30% MeOH)

Sources & evidence

ORD record
ord-b5f4baf754a54f91a4beaddd3f28f3dd
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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