2-Ethoxyethyl 4-methylbenzene-1-sulfonate → N-(2-ethoxyethyl)-2,3,6-trimethyl-aniline

HRID 1834344Notes

Reaction equation

HRID 1834344 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5]OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:2].[CH3:17][C:18]1[C:24]([CH3:25])=[CH:23][CH:22]=[C:21]([CH3:26])[C:19]=1[NH2:20]>C1(C)C=CC=CC=1>[CH2:1]([O:3][CH2:4][CH2:5][NH:20][C:19]1[C:21]([CH3:26])=[CH:22][CH:23]=[C:24]([CH3:25])[C:18]=1[CH3:17])[CH3:2]

Participants

4

Reactant 2

HCID 41253902-Ethoxyethyl 4-methylbenzene-1-sulfonateHCID 119589472,3,6-Trimethylaniline

Product 1

HCID 20372930N-(2-ethoxyethyl)-2,3,6-trimethyl-anilineYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to the method of Example 1a 553 g (2.26 moles) of p-toluenesulfonic-acid-(2-ethoxyethyl)-ester are added to a solution of 607 g (4.5 moles) 2,3,6-trimethylaniline in 1 liter of toluene. 317 g(68% of theoretical amount) of N-(2-ethoxyethyl)-2,3,6-trimethyl-aniline are obtained, b.p. 150°-152° C / 14 Torr.

Sources & evidence

ORD record
ord-caa390664d4a4a9691be0a7522983a09
Source dataset
uspto-grants-1978_01
Patent number
US04070179

Reaction notes

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