Nitrourea → HCID 67885413, compound

HRID 2081407Notes

Reaction equation

HRID 2081407 reaction equation
[CH3:1][C@H:2]1[C@H:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:4][NH:3]1.[N+]([NH:20][C:21](N)=[O:22])([O-])=O>CC(C)=O.O>[CH3:1][C@H:2]1[C@H:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=2)[CH2:4][N:3]1[C:21]([NH2:20])=[O:22]

Participants

5

Reactant 2

HCID 62372NitroureaHCID 67885882HCID 67885882, compound

Product 1

HCID 67885413HCID 67885413, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A mixture of 6 g (0.015 mole) of crude trans-2-methyl-3-[3-(trifluoromethyl)phenoxy]azetidine (purity 56.6% contains diphenylmethane) and 2.4 g (0.0225 mole) of nitrourea in 40 ml of acetone was treated with 4 ml of water, then heated until a clear homogenous solution was obtained. The reaction mixture was stirred overnight as it cooled to ambient temperature and diluted with water until an oil separated. The oil solidified and was recrystallized from ethanol/water, yielding 4.3 g of white plate-like crystals; m.p. 117°-118° C. The product was recrystallized from benzene, yielding 3.35 g (96.8%) of crystals, m.p. 118°-119° C.

Workup

  1. temperatureheated until a clear homogenous solution
  2. customwas obtained
  3. customseparated
  4. customwas recrystallized from ethanol/water
  5. customyielding 4.3 g of white plate-like crystals
  6. customThe product was recrystallized from benzene

Sources & evidence

ORD record
ord-e6a8da2f62f34e01960c405956c82c5a
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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