2-Nitrobenzenesulfonyl chloride → N-cyclopropyl-2-nitrobenzenesulfonamide

HRID 1835833Notes

Reaction equation

HRID 1835833 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[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>[CH:1]1([NH:4][S:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N+:5]([O-:7])=[O:6])(=[O:15])=[O:16])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 69828Cyclopropylamine

Product 1

HCID 796630N-cyclopropyl-2-nitrobenzenesulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −78° C. mixture of cyclopropylamine (10 g, 1.75 mmol) in CH2Cl2 (100 mL) was added a solution of 2-nitrobenzene sulfonyl chloride (22.1 g, 85.7 mmol) and the mixture was stirred for 12 h. The mixture was washed with 1N HCl dried over MgSO4 then concentrated to give 18.7 g, (88%) of a N-Cyclopropyl-2-nitro-benzenesulfonamide as a tan solid.

Workup

  1. washThe mixture was washed with 1N HCl
  2. dry with materialdried over MgSO4
  3. concentrationthen concentrated

Sources & evidence

ORD record
ord-e86f6a80d083437cace06a510a77b434
Source dataset
uspto-grants-2004_08
Patent number
US06774134B2

Reaction notes

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