Phosgene → HCID 15042232, compound

HRID 2371725Notes

Reaction equation

HRID 2371725 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:11][C:12]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[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]=[CH:34][C:33]([C:36]([F:37])([F:39])[F:38])=[CH:32][C:13]=1[O:14][CH:15]1[CH2:16][N:17]([C:1]([Cl:4])=[O:2])[CH2:18]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 15042225HCID 15042225, compound

Product 1

HCID 15042232HCID 15042232, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 13.5 g (0.14 mol) of phosgene and 19.4 g (0.14 mol) of potassium carbonate in 300 mL of methylene chloride was stirred under nitrogen while cooling in an ice bath. The cold reaction mixture was treated with a solution of 47.6 g (0.114 mol) of 3-[2-chloro-5-(trifluoromethyl)phenoxy]-1-(diphenylmethyl)azetidine in 100 mL of methylene chloride added dropwise. After stirring for 16 hr as the reaction mixture warmed to ambient temperature, it was again cooled in an ice bath while small pieces of ice were added to destroy the excess phosgene. The methylene chloride solution was decanted from the inorganic salt paste, dried by filtering through Whatman PS paper and concentrated in vacuo (58 g). The residue was triturated with 600 mL (3×200 mL) of petroleum ether, decanting the petroleum ether each time. The residue was then triturated with boiling hexanes and allowed to cool. The insoluble oil was separated using a separating funnel yielding 24 g of oily product (67%). A sample was distilled in a Kugelrohr apparatus (136°-150° C. @ 2 mm Hg) yielding a clear oil which slowly solidified on standing, mp 40°-45°.

Workup

  1. temperaturewhile cooling in an ice bath
  2. customThe cold reaction mixture
  3. additionadded dropwise
  4. stirringAfter stirring for 16 hr as the reaction mixture
  5. temperatureit was again cooled in an ice bath while small pieces of ice
  6. additionwere added
  7. customto destroy the excess phosgene
  8. customThe methylene chloride solution was decanted from the inorganic salt paste
  9. customdried
  10. filtrationby filtering through Whatman PS paper
  11. concentrationconcentrated in vacuo (58 g)
  12. customThe residue was triturated with 600 mL (3×200 mL) of petroleum ether
  13. customdecanting the petroleum ether each time
  14. customThe residue was then triturated with boiling hexanes
  15. temperatureto cool
  16. customThe insoluble oil was separated

Sources & evidence

ORD record
ord-eeeb0234e5554726b45cac9a07825fc0
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Reaction notes

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