Water → HCID 67885771, compound

HRID 2081406Notes

Reaction equation

HRID 2081406 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.[CH3:17][N:18]=[C:19]=[O:20].O>O1CCCC1>[CH3:17][NH:18][C:19]([N:3]1[CH2:4][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)[C@@H:2]1[CH3:1])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 12228Methyl IsocyanateHCID 67885882HCID 67885882, compound

Product 1

HCID 67885771HCID 67885771, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 6 g (0.015 mole) of crude trans-2-methyl-3-[3-(trifluoromethyl)phenoxy]azetidine in 50 ml of tetrahydrofuran was treated with 0.94 g (0.0165 mole) of methyl isocyanate added dropwise and stirred for 16 hr under a blanket of nitrogen. Dilution of the reaction mixture with water produced an oil which solidified. After decanting the aqueous tetrahydrofuran phase, the solid residue was recrystallized from ethanol-water to yield 3.95 g (91.4%) of fine white crystals, m.p. 104.5°-106° C.

Workup

  1. additionadded dropwise
  2. customAfter decanting the aqueous tetrahydrofuran phase
  3. customthe solid residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-acb37e06837e416b9cb23b56e9769754
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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