2-Methoxyethylamine → HCID 53647392, compound

HRID 1388991Notes

Reaction equation

HRID 1388991 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[CH3:24][O:25][CH2:26][CH2:27][NH2:28].C(N(CC)CC)C>C(Cl)Cl>[CH3:24][O:25][CH2:26][CH2:27][NH:28][C:14](=[O:15])[CH:13]([O:12][C:11]1[CH:18]=[CH:19][C:8]([O:7][C:6]2[CH:20]=[CH:21][C:3]([C:2]([F:23])([F:22])[F:1])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1)[CH3:17]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 129060152-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propanoyl chloride

Product 1

HCID 53647392HCID 53647392, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While cooling with ice, 17.2 g (0.05 mole) of α-[4-(p-trifluoromethylphenoxy)-phenoxy]-propionyl chloride are added dropwise to a mixture of 4.1 g (0.055 mole) of 2-methoxyethylamine, 7.5 ml (0.055 mole) of triethylamine and 50 ml of methylene chloride, and the temperature is allowed to rise to 20° C. The reaction mixture is stirred for 2 hours, then concentrated. The residue is filtered in ether over a small column of silica gel. Concentration of the filtrate affords 14.9 g (77.6%) of α-[4-(p-trifluoromethylphenoxy)-phenoxy]-propionic acid (2-methoxy)-ethylamide with a melting point of 73°-75° C.

Workup

  1. customto rise to 20° C
  2. concentrationconcentrated
  3. filtrationThe residue is filtered in ether over a small column of silica gel

Sources & evidence

ORD record
ord-1321779db9f44a28b410e4e143406039
Source dataset
uspto-grants-1981_01
Patent number
US04243410

Reaction notes

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