Ammonium Hydroxide → 3-(2-Chloro-6-methylphenoxy)-1-azetidinecarboxamide

HRID 2371744Notes

Reaction equation

HRID 2371744 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.[OH-].[NH4+: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]([NH2:18])=[O:10])[CH2:6]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 150422313-(2-Chloro-6-methylphenoxy)-1-azetidinecarbonyl chloride

Product 1

HCID 199062253-(2-Chloro-6-methylphenoxy)-1-azetidinecarboxamideYield 77.6%

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 2.8 mL (0.045 mole) of 57% ammonium hydroxide. After stirring for 72 h the reaction mixture was diluted with 200 mL of water and the precipitated product collected by filtration (3.6 g of pale yellow product). Recrystallization from benzene yielded 2.8 g (69.2%) of fine white crystals, mp 256°-157° C.

Workup

  1. filtrationthe precipitated product collected by filtration (3.6 g of pale yellow product)
  2. customRecrystallization from benzene

Sources & evidence

ORD record
ord-a146e8d89a734345986151fd9987599c
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Reaction notes

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