Water → 3-[4-(Trifluoromethyl)phenoxy]azetidine-1-carboxamide

HRID 1886624Notes

Reaction equation

HRID 1886624 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.[N+]([NH:19][C:20](N)=[O:21])([O-])=O.O>CC(C)=O>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([O:7][CH:8]2[CH2:9][N:10]([C:20]([NH2:19])=[O:21])[CH2:11]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 62372NitroureaHCID 128124993-[4-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 135657923-[4-(Trifluoromethyl)phenoxy]azetidine-1-carboxamideYield 55.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 9.6 g (0.025 mole) of 3-[4-(trifluoromethyl)phenoxy]azetidine 56.66% (contains diphenylmethane) in 50 ml of acetone was treated with 4.22 g (0.045 mole) of nitrourea and 5 ml of water. The mixture was heated on a hot plate until a clear solution was obtained then allowed to cool to ambient temperature during the next 4 hr. The reaction mixture was diluted with 200 ml of ice water and an oil separated (diphenylmethane) which was dissolved in 30/60 petroleum ether and separated. Upon standing, a fine white precipitate formed in the aqueous solution. Filtration yielded 3.6 g of fine white crystals, m.p. 176°-178° C. After drying under 0.5 mm Hg vacuum at 80° C., the product weight was reduced to 3.1 g (47.7%), m.p. 178°-179° C.

Workup

  1. temperatureThe mixture was heated on a hot plate until a clear solution
  2. customwas obtained
  3. customan oil separated (diphenylmethane) which
  4. dissolutionwas dissolved in 30/60 petroleum ether
  5. customseparated
  6. customa fine white precipitate formed in the aqueous solution
  7. filtrationFiltration

Sources & evidence

ORD record
ord-489b5915890b4a19b12354cb5188b3e2
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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