Ethyl isocyanate → N-Ethyl-3-[4-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

HRID 2081425Notes

Reaction equation

HRID 2081425 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([O:7][CH:8]2[CH2:11][NH:10][CH2:9]2)=[CH:5][CH:4]=1.[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17]>C(OC(C)C)(C)C>[CH2:16]([NH:18][C:19]([N:10]1[CH2:9][CH:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:13][CH:12]=2)[CH2:11]1)=[O:20])[CH3:17]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 128124993-[4-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 19799590N-Ethyl-3-[4-(trifluoromethyl)phenoxy]-1-azetidinecarboxamideYield 42.8%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A solution of 6.5 g (0.03 mole) of crude 3-[4-(trifluoromethyl)phenoxy]azetidine in 50 ml of isopropyl ether was stirred under a blanket of nitrogen while 2.85 g (0.04 mole) of ethyl isocyanate was added dropwise. After stirring for 2 hr at ambient temperature, a solid began to precipitate, and after 4 hr, the solid was collected by filtration to yield 3.7 g of beige product, m.p. 94°-96° C. Rework of the filtrate gave only a trace of additional product. The product was recrystallized from isopropyl ether/hexane (treated with charcoal) to yield 2.61 g (30%) of product, m.p. 109°-110° C.

Workup

  1. additionwas added dropwise
  2. customto precipitate
  3. waitafter 4 hr
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-62053d83654f4e7c92e967b7cac2377b
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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