Dimethylamine → Dimethyl-[2-(3-nitro-benzenesulfonyl)-ethyl]-amine

HRID 1957978Notes

Reaction equation

HRID 1957978 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14]O)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:16][NH:17][CH3:18]>C(O)C.ClCCl>[CH3:16][N:17]([CH3:18])[CH2:14][CH2:13][S:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 170561Ethanol, 2-[(3-nitrophenyl)sulfonyl]-

Product 1

HCID 68425174Dimethyl-[2-(3-nitro-benzenesulfonyl)-ethyl]-amineYield 59.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-(3-Nitro-phenylsulfonyl)-ethanol (0.5 g; 2.6 mmol) was dissolved in 3 mL ethanol and 2 mL of dichloromethane. Then 1 mL of (7.8 mmol) dimethylamine (33% in ethanol) was added, the reaction mixture was subsequently concentrated in vacuo, dissolved in dichloromethane, and the product was precipitated by adding diethyl ether and petrol ether. 0.4 g (1.55 mmol; 59% yield) of dimethyl-[2-(3-nitro-benzenesulfonyl)-ethyl]-amine were obtained as a yellow solid.

Workup

  1. concentrationthe reaction mixture was subsequently concentrated in vacuo
  2. dissolutiondissolved in dichloromethane
  3. customthe product was precipitated
  4. additionby adding diethyl ether and petrol ether

Sources & evidence

ORD record
ord-201a381533a24327bfc9497915fbee9a
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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