Phosgene → 1-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

HRID 1886583Notes

Reaction equation

HRID 1886583 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].C1(C(C2C=CC=CC=2)[N:18]2[CH2:21][CH:20]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH2:19]2)C=CC=CC=1>C(Cl)Cl>[F:32][C:29]([F:30])([F:31])[C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[O:22][CH:20]1[CH2:21][N:18]([C:1]([Cl:4])=[O:2])[CH2:19]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 117286941-Benzhydryl-3-[3-(trifluoromethyl)phenoxy]azetidine

Product 1

HCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidineYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 35.6 g (0.36 mole) of phosgene in 200 ml of methylene chloride at 5° C. was stirred with 50 g (0.36 mole) of potassium carbonate for 1 hr. To the mixture was added dropwise 115 g (0.3 mole) of 1-diphenylmethyl-3-[3-(trifluoromethyl)phenoxy]azetidine in 400 ml of methylene chloride. After stirring for 18 hr, the reaction mixture was filtered and the filtrate was washed with water, dried over magnesium sulfate and concentrated on a rotary evaporator to a viscous oil residue, 133.2 g. Trituration of the residue with hexane gave a solid which was recrystallized from cold hexane to yield 52 g (62%) of white crystals, m.p. 72.5°-74° C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe filtrate was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator to a viscous oil residue, 133.2 g
  5. customTrituration of the residue with hexane gave a solid which
  6. customwas recrystallized from cold hexane

Sources & evidence

ORD record
ord-f3695dcf940547f1b2fc844941b79ed8
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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