Triethylamine → N-(4-Nitrobenzyl)cyclopropanesulfonamide

HRID 1025515

Reaction equation

HRID 1025515 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH:13]1([S:16](Cl)(=[O:18])=[O:17])[CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl.Cl.O>[CH:13]1([S:16]([NH:10][CH2:9][C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:12][CH:11]=2)(=[O:18])=[O:17])[CH2:15][CH2:14]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 66910210N-(4-Nitrobenzyl)cyclopropanesulfonamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Nitrobenzylamine HCl (1.5 g), cyclopropanesulfonyl chloride (1 g) and triethylamine (3 mL) were dissolved in dichloromethane (20 mL). The reaction solution was stirred at rt overnight. The reaction mixture was diluted with 1N HCl aq. solution (50 mL) and water (100 mL). The solution was extracted with ethyl acetate (2×100 mL). The organic solution was evaporated to give N-cyclopropylsulfonyl-4-nitrobenzylamine. 1H NMR (DMSO-d6): δ 0.89 (d, 7.8 Hz, 4H), 4.33 (d, J=6.6 Hz, 2H), 7.61 (d, J=8.7 Hz, 2H), 7.83 (t, J=6.6 Hz, 1H), 8.20 (d, 8.7 Hz, 2H).

Workup

  1. extractionThe solution was extracted with ethyl acetate (2×100 mL)
  2. customThe organic solution was evaporated

Sources & evidence

ORD record
ord-2c17ff719c16403c99b84115dd8e943e
Source dataset
uspto-grants-2014_05
Patent number
US08729087B2

Linked notes

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