Nitrourea → HCID 67885413, compound

HRID 1032117Notes

Reaction equation

HRID 1032117 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-065a556c239a4300a8628ba689cf9fe9
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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