Phenyl isocyanate → HCID 15053429, compound

HRID 2081404Notes

Reaction equation

HRID 2081404 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:21])([F:20])[C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[O:12][CH:13]1[CH2:16][NH:15][CH2:14]1.C(N(CC)CC)C.[C:29]1([N:35]=[C:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1.O>[C:29]1([NH:35][C:36]([N:15]2[CH2:16][CH:13]([O:12][C:11]3[CH:17]=[CH:18][CH:19]=[C:9]([C:8]([F:7])([F:20])[F:21])[CH:10]=3)[CH2:14]2)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 19799580HCID 19799580, compound

Product 1

HCID 15053429HCID 15053429, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred slurry of 6.2 g (0.02 mole) of 3-[3-(trifluoromethyl)phenoxy]azetidine oxalate in 60 ml of tetrahydrofuran was treated with 5 ml of triethylamine followed by 2.62 g (0.022 mole) of phenyl isocyanate and stirring continued for 16 hr. The reaction mixture was diluted with water until an oil separated which quickly solidified. The aqueous tetrahydrofuran was decanted and the solid residue recrystallized from ethanol-water to yield 5.3 g (80.1%) of white crystals, m.p. 137°-138° C.

Workup

  1. customseparated which
  2. customThe aqueous tetrahydrofuran was decanted
  3. customthe solid residue recrystallized from ethanol-water

Sources & evidence

ORD record
ord-94e655bc0345497db43a22037dd48f9e
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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