Phosgene → 3-(2-Chloro-4-fluorophenoxy)-1-azetidinecarbonyl chloride

HRID 2371728

Reaction equation

HRID 2371728 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:11][C:12]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:13]=1[O:14][CH:15]1[CH2:18][N:17](C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:16]1>C(Cl)Cl>[Cl:11][C:12]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:13]=1[O:14][CH:15]1[CH2:18][N:17]([C:1]([Cl:4])=[O:2])[CH2:16]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 150422263-(2-Chloro-4-fluorophenoxy)-1-(diphenylmethyl)azetidine

Product 1

HCID 150422343-(2-Chloro-4-fluorophenoxy)-1-azetidinecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred solution of 9.0 g (0.09 mole) of phosgene in 200 mL of methylene chloride under nitrogen was treated with 12.5 g (0.09 mole) of anhydrous potassium carbonate and stirred for 30 min. The reaction mixture was cooled in an ice bath while 28 g (0.08 mole) of 3-(2-chloro-4-fluorophenoxy)-1-(diphenylmethyl)azetidine in 100 mL of methylene chloride was added dropwise. After stirring for 16 hr at ambient temperature the reaction mixture was cooled to 0° C. in an ice water bath and small pieces of ice were added to destroy the excess phosgene, being careful to control the evolution of carbon dioxide gas. When the evolution of gas ceased, the reaction mixture was decanted from the inorganic slurry, dried (filtered through Whatman PS paper) and concentrated in vacuo, 41.9 g. Upon standing, a semisolid residue formed and the solid was collected by filtration after trituration with hexane to obtain 13.2 g (62.5%). A sample was recrystallized from hexane for analysis yielding fine white crystals, mp 93°-94° C.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring for 16 hr at ambient temperature the reaction mixture
  3. additionsmall pieces of ice were added
  4. customto destroy the excess phosgene
  5. customthe reaction mixture was decanted from the inorganic slurry
  6. customdried
  7. filtration(filtered through Whatman PS paper)
  8. concentrationconcentrated in vacuo, 41.9 g
  9. customa semisolid residue formed
  10. filtrationthe solid was collected by filtration after trituration with hexane
  11. customto obtain 13.2 g (62.5%)
  12. customA sample was recrystallized from hexane for analysis
  13. customyielding fine white crystals, mp 93°-94° C.

Sources & evidence

ORD record
ord-4d6ddf24693243aebde1c9b1fa6f28f8
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Linked notes

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