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

HRID 903131

Reaction equation

HRID 903131 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.[OH-].[K+].[CH3:24][N:25]=[C:26]=[O:27]>C1C=CC=CC=1>[CH3:24][NH:25][C:26]([N:16]1[CH2:15][CH:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([C:8]([F:7])([F:20])[F:21])=[CH:19][CH:18]=2)[CH2:17]1)=[O:27]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 12228Methyl IsocyanateHCID 14797Potassium HydroxideHCID 128124993-[4-(Trifluoromethyl)phenoxy]azetidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The oxalic acid salt of 3-(4-trifluoromethylphenoxy) azetidine (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 over calcium sulfate and filtered, and to the stirring dried benzene solution was added 2.6 g. (0.046 mole) of methyl-isocyanate. Stirring was continued overnight. The mixture was concentrated at reduced pressure and the solid residue was recrystallized from a mixture of isopropyl ether-ethyl acetate. The product weighed 7.5 g. (65%) and melted at 154°-157° C.

Workup

  1. dry with materialThe benzene layer was dried over calcium sulfate
  2. filtrationfiltered
  3. additionto the stirring dried benzene solution was added 2.6 g
  4. concentrationThe mixture was concentrated at reduced pressure
  5. customthe solid residue was recrystallized from a mixture of isopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-05ba8cda715a4cb3864f6eec80ea4e74
Source dataset
uspto-grants-1980_10
Patent number
US04226861

Linked notes

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