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

HRID 2081387Notes

Reaction equation

HRID 2081387 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 recrystalized 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 recrystalized from cold hexane

Sources & evidence

ORD record
ord-38c2d2bdb5224fd884dc59e8f1deb8d8
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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