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Triethylamine → N-(4-Nitrobenzyl)cyclopropanesulfonamide

HRID 215906
Notes
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Reaction equation

HRID 215906 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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, J=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, J=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-c45a3674109a4c44b5c1ca0dd7b9d6c8
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193197B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes