Oxalic Acid → 3-(4-Trifluoromethylphenoxy)-N-methyl-1-azetidinecarboxamide

HRID 2371737Notes

Reaction equation

HRID 2371737 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:21])([F:20])[C:9]1[CH:19]=[CH:18][C:12]([O:13][CH:14]2[CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.[CH3:22][N:23]=[C:24]=[O:25]>>[F:21][C:8]([F:7])([F:20])[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH:14]2[CH2:15][N:16]([C:24]([NH:23][CH3:22])=[O:25])[CH2:17]2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 971Oxalic AcidHCID 12228Methyl IsocyanateHCID 128124993-[4-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 134201663-(4-Trifluoromethylphenoxy)-N-methyl-1-azetidinecarboxamide

Procedure

The oxalic acid salt of 3-[4-(trifluoromethyl)phenoxy]azetidine, weighing 13.0 g (0.042 mole), was partitioned between 50 ml of benzene and 50 ml of potassium hydroxide solution. The benzene layer was dried with Drierite and filtered, and to this stirring filtrate was added 2.6 g (0.046 mole) of methyl isocyanate. Stirring was continued overnight. The mixture was concentrated in vacuo, and the solid residue was recrystallized from a mixture of isopropyl ether-ethyl acetate to give 7.5 g (65%), mp 154°-157°.

Workup

  1. customwas partitioned between 50 ml of benzene and 50 ml of potassium hydroxide solution
  2. dry with materialThe benzene layer was dried with Drierite
  3. filtrationfiltered
  4. concentrationThe mixture was concentrated in vacuo
  5. customthe solid residue was recrystallized from a mixture of isopropyl ether-ethyl acetate
  6. customto give 7.5 g (65%), mp 154°-157°

Sources & evidence

ORD record
ord-bc8233dc8c6a4175968bd6a8804f188f
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Reaction notes

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