Dimethylamine → N,N-dimethyl-4-nitrobenzenesulfonamide

HRID 1484831

Reaction equation

HRID 1484831 reaction equation
[CH3:1][NH:2][CH3:3].CCN(C(C)C)C(C)C.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C(Cl)Cl>[CH3:1][N:2]([CH3:3])[S:22]([C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=1)(=[O:23])=[O:24]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 2747580N,N-dimethyl-4-nitrobenzenesulfonamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of dimethylamine (284 mg, 6.3 mmol, 1.5 equiv.) and DIPEA (1 mL) in DCM (15 mL) was added dropwise a solution of 4-nitrobenzene-1-sulfonyl chloride (800 mg, 4.2 mmol, 1.0 equiv.) in DCM (5 mL). The reaction mixture was stirred at room temperature for 2 h. Then, the reaction mixture was washed with water and brine. The organic layers was dried (Na2SO4) and concentrated to get the residue, which was washed with isopropyl ether to afford compound N,N-dimethyl-4-nitrobenzenesulfonamide (879 mg, 91%).

Workup

  1. washThen, the reaction mixture was washed with water and brine
  2. dry with materialThe organic layers was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto get the residue, which
  5. washwas washed with isopropyl ether

Sources & evidence

ORD record
ord-bb57abf62e43442b94674328fd6e7599
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Linked notes

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