Triethylamine → 3-(3-Fluorophenoxy)-1-azetidinecarboxamide

HRID 974596Notes

Reaction equation

HRID 974596 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[O:11][CH:12]1[CH2:15][NH:14][CH2:13]1.C(N(CC)CC)C.[N+]([NH:29][C:30](N)=[O:31])([O-])=O>CC(C)=O.O>[F:7][C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=1)[O:11][CH:12]1[CH2:15][N:14]([C:30]([NH2:29])=[O:31])[CH2:13]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62372NitroureaHCID 197995893-(3-Fluorophenoxy)azetidine oxalate

Product 1

HCID 150534343-(3-Fluorophenoxy)-1-azetidinecarboxamideYield 43.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A stirred slurry of 3 g (0.012 mole) of 3-(3-fluorophenoxy)azetidine oxalate [1:1] in 20 ml of acetone was treated with 3 ml of triethylamine and stirred for 1 hr. The resulting solution was treated with 2.5 g (0.024 mole) of nitrourea and 2 ml of water then stirred for 16 hr. The reaction mixture was diluted with water and the product crystallized. Recrystallization from methanol-water yielded 1.1 g (43.6%) of a white crystalline solid, m.p. 169°-170° C.

Workup

  1. stirringthen stirred for 16 hr
  2. customthe product crystallized
  3. customRecrystallization from methanol-water

Sources & evidence

ORD record
ord-d53519856aa64611aa59492c8ffa88df
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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