Dimethylamine → 4-(4-Dimethylaminosulfonylbenzyl)-nitrobenzene

HRID 634811Notes

Reaction equation

HRID 634811 reaction equation
[CH3:1][NH:2][CH3:3].ClCCl.Cl[S:8]([C:11]1[CH:26]=[CH:25][C:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9]>O1CCCC1>[CH3:1][N:2]([CH3:3])[S:8]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)=[CH:25][CH:26]=1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 218769754-(4-Chlorosulfonylbenzyl)-nitrobenzene dichloromethane

Product 1

HCID 218769584-(4-Dimethylaminosulfonylbenzyl)-nitrobenzeneYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of dimethylamine in tetrahydrofuran (2M, excess) was added 4-(4-chlorosulfonylbenzyl)-nitrobenzene dichloromethane hemisolvate (354 mg, 1 mmol) dissolved in tetrahydrofuran (5 mL). The mixture was stirred for 1 hour and extracted with a solution of diethyl ether and dilute potassium carbonate. The organic layer was separated and solvents evaporated. The residue was recrystallized from acetone/hexanes to give 4-(4-dimethylaminosulfonylbenzyl)-nitrobenzene (311 mg, 98%).

Workup

  1. extractionextracted with a solution of diethyl ether and dilute potassium carbonate
  2. customThe organic layer was separated
  3. customsolvents evaporated
  4. customThe residue was recrystallized from acetone/hexanes

Sources & evidence

ORD record
ord-09bdd69dbb674d3e90befe97e88a9051
Source dataset
uspto-grants-2001_02
Patent number
US06184242B2

Reaction notes

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