Phenyl isocyanate → HCID 15053430, compound

HRID 974566Notes

Reaction equation

HRID 974566 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:21])([F:20])[C:9]1[CH:19]=[CH:18][C:12]([O:13][CH:14]2[CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>O1CCCC1.O>[C:22]1([NH:28][C:29]([N:16]2[CH2:15][CH:14]([O:13][C:12]3[CH:11]=[CH:10][C:9]([C:8]([F:7])([F:20])[F:21])=[CH:19][CH:18]=3)[CH2:17]2)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 128125003-[4-(Trifluoromethyl)phenoxy]azetidine oxalate

Product 1

HCID 15053430HCID 15053430, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred slurry of 6.2 g (0.02 mole) of 3-[4-(trifluoromethyl)phenoxy]azetidine oxalate and 2.62 g (0.022 mole) of phenyl isocyanate in 60 ml of tetrahydrofuran was treated with 5 ml of triethylamine and stirring continued for 16 hr. The reaction mixture was diluted with water until an oil separated. The tetrahydrofuran-water portion was decanted and the residue solidified on standing. Recrystallization from ethanol-water yielded 3.5 g (53.4%) of fine white crystals, m.p. 174.5°-176° C.

Workup

  1. customseparated
  2. customThe tetrahydrofuran-water portion was decanted
  3. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-1fb65e83a30a4700b86d863e8c5878c2
Source dataset
uspto-grants-1991_11
Patent number
US05068231

Reaction notes

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