Methylamine → 3-(2-Chloro-6-methyphenoxy)-N-methyl-1-azetidinecarboxamide

HRID 2371746Notes

Reaction equation

HRID 2371746 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9](Cl)=[O:10])[CH2:6]1.[CH3:17][NH2:18]>O1CCCC1.O>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9]([NH:18][CH3:17])=[O:10])[CH2:6]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 150422313-(2-Chloro-6-methylphenoxy)-1-azetidinecarbonyl chloride

Product 1

HCID 678545833-(2-Chloro-6-methyphenoxy)-N-methyl-1-azetidinecarboxamideYield 146.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 3.9 g (0.015 mole) of 3-(2-chloro-6-methylphenoxy)-1-azetidinecarbonyl chloride in 20 mL of tetrahydrofuran was treated all at once with 3.5 mL (0.045 mole) of 40% aqueous monomethylamine. After stirring for 72 h the reaction mixture was diluted with 200 mL of water and the precipitated solid collected by filtration to give 5.6 g of wet white product. The crude product was recrystallized (after drying) from benzene/ligroin, yielding 2.9 g (75.9%) of white crystalline product, mp 119°-121° C.

Workup

  1. filtrationthe precipitated solid collected by filtration

Sources & evidence

ORD record
ord-3f97c31afe4e48569fe37c41c23822df
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Reaction notes

Loading…