Triethylamine → N-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-3-(methylsulfonyl)propionamide

HRID 652277Notes

Reaction equation

HRID 652277 reaction equation
[CH2:1]([O:3][CH2:4][CH:5]([OH:15])[CH2:6][O:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[CH3:2].C(N(CC)CC)C.[CH3:23][S:24]([CH2:27][CH2:28][C:29](Cl)=[O:30])(=[O:26])=[O:25]>ClCCl>[CH2:1]([O:3][CH2:4][CH:5]([OH:15])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH:12][C:29](=[O:30])[CH2:28][CH2:27][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:13][CH:14]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107748571-(4-Aminophenoxy)-3-ethoxypropan-2-olHCID 201998553-(Methylsulfonyl)propionyl chloride

Product 1

HCID 13657123N-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-3-(methylsulfonyl)propionamideYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.11 g quantity of 4-(3-ethoxy-2-hydroxypropoxy)aniline and 1.53 g of triethylamine were dissolved in 50 ml of dichloromethane. To the solution was added 1.71 g of 3-(methylsulfonyl)propionyl chloride with ice cooling. The same subsequent procedure as in Example 2 was repeated and recrystallization from benzene was performed, giving 3.25 g of N-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-3-(methylsulfonyl)propionamide in a yield of 94.2 %. M.p. 111° to 112° C.

Workup

  1. customrecrystallization from benzene

Sources & evidence

ORD record
ord-6892363b853443e7aa0580139f31fe9f
Source dataset
uspto-grants-1987_06
Patent number
US04670583

Reaction notes

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