Dimethylamine → N,N-Dimethyl-3-(4-nitrophenyl)prop-2-yn-1-amine

HRID 24933Notes

Reaction equation

HRID 24933 reaction equation
[CH3:1][NH:2][CH3:3].C1(C)C=CC(S(O[CH2:14][C:15]#[C:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)(=O)=O)=CC=1>ClCCl>[CH3:1][N:2]([CH3:3])[CH2:14][C:15]#[C:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 225692544-[3-(p-Tolylsulphonyloxy)-prop-1-ynyl]-nitrobenzene

Product 1

HCID 22569284N,N-Dimethyl-3-(4-nitrophenyl)prop-2-yn-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

190 ml (4.2 mmol) of dimethylamine dissolved in 2.5 ml of dichloromethane are added dropwise at 0° C. to a solution of 0.7 g (2.1 mmol) of 4-[3-(p-tolylsulphonyloxy)-prop-1-ynyl]-nitrobenzene in 10 ml of dichloromethane. The cooling is stopped and the mixture is stirred for 18 hours at ambient temperature. Then the reaction solution is washed with water and freed from solvent. The residue is chromatographed on silica gel (dichloromethane/methanol=10:1). The product is obtained as an oil.

Workup

  1. washThen the reaction solution is washed with water
  2. customThe residue is chromatographed on silica gel (dichloromethane/methanol=10:1)
  3. customThe product is obtained as an oil

Sources & evidence

ORD record
ord-15b55c7d2fd64ecbb6bbe60feb3c7821
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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