Nitrourea → Dezinamide

HRID 1886617Notes

Reaction equation

HRID 1886617 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][NH:9][CH2:8]1.[N+]([NH:19][C:20](N)=[O:21])([O-])=O>CC(C)=O>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][N:9]([C:20]([NH2:19])=[O:21])[CH2:8]1

Participants

4

Reactant 2

HCID 62372NitroureaHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidine

Product 1

HCID 146291Dezinamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 30.6 g (0.141 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine and 42 g (0.321 mole) of nitrourea (80%) in 500 ml of acetone was stirred for 5 days (5 days not required, but convenient) at room temperature. The mixture was filtered and the filtrate concentrated in vacuo. The residue was partitioned between 150 ml of water and 100 ml of ethyl acetate and the layers separated. The aqueous layer was washed with 100 ml of ethyl acetate. The ethyl acetate layers were washed with 75 ml of 5% aqueous sodium hydroxide solution followed by 75 ml of water, dried over sodium sulfate and concentrated in vacuo. The residual oil was crystallized from ethyl alcohol-ethyl acetate to give 22 g (60%) substantially the title compound. Recrystallization twice from ethyl alcohol gave 9.9 g of white crystalline solid, m.p. 151°-152.5° C.

Workup

  1. customat room temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was partitioned between 150 ml of water and 100 ml of ethyl acetate
  5. customthe layers separated
  6. washThe aqueous layer was washed with 100 ml of ethyl acetate
  7. washThe ethyl acetate layers were washed with 75 ml of 5% aqueous sodium hydroxide solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residual oil was crystallized from ethyl alcohol-ethyl acetate

Sources & evidence

ORD record
ord-2eb0e44d52d74a1f8a07031fc968f28b
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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