Triethylamine → N-(2-Chloropropyl)-N,2,6-trimethylbenzenamine

HRID 1649976Notes

Reaction equation

HRID 1649976 reaction equation
CS([Cl:5])(=O)=O.[CH3:6][N:7]([CH2:16][CH:17](O)[CH3:18])[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15].C(N(CC)CC)C>ClCCCl>[CH3:6][N:7]([CH2:16][CH:17]([Cl:5])[CH3:18])[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13674770HCID 13674770, compound

Product 1

HCID 13674775N-(2-Chloropropyl)-N,2,6-trimethylbenzenamineYield 90.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3.1 ml (4.6 g, 40 mmoles) of methanesulfonyl chloride are added dropwise, at a temperature not exceeding 20° C., to a solution of 7.0 g (36.2 mmoles) of 1-[N-methyl-N-(2,6-dimethylphenyl)-amino]-2-propanol and 5.45 ml (4.0 g, 40 mmoles) of triethyl amine in 50 ml of 1,2-dichloroethane, and the resulting mixture is stirred at room temperature for 3 hours. The mixture is washed then thrice with 30 ml of water, each, dried over anhydrous magnesium sulfate, the solvent is evaporated, and the oily residue is distilled under reduced pressure. 6.9 g (90.2%) of 1-[N-methyl-N-(2,6-dimethylphenyl)-amino]-2-chloro-propane are obtained; b.p.: 116°-118° C./133 Pa.

Workup

  1. washThe mixture is washed
  2. dry with materialeach, dried over anhydrous magnesium sulfate
  3. customthe solvent is evaporated
  4. distillationthe oily residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-92a3d90499da4f74afd93da2aa61e499
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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