Phosgene → HCID 15053365, compound

HRID 1886576Notes

Reaction equation

HRID 1886576 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].[Br:11][C:12]1[CH:13]=[C:14]([CH:33]=[CH:34][CH:35]=1)[O:15][CH:16]1[CH2:19][N:18](C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:17]1>C(Cl)Cl>[Br:11][C:12]1[CH:13]=[C:14]([CH:33]=[CH:34][CH:35]=1)[O:15][CH:16]1[CH2:19][N:18]([C:1]([Cl:4])=[O:2])[CH2:17]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 15053370HCID 15053370, compound

Product 1

HCID 15053365HCID 15053365, compoundYield 175.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 22.7 g (0.23 mole) of phosgene in 200 ml of methylene chloride was treated with 29 g (0.23 mole) of potassium carbonate, stirred for 30 min, then 75.4 g (0.19 mole) of 3-(3-bromophenoxy)-1-diphenylmethylazetidine in 150 ml of methylene chloride was added dropwise. After stirring for 5 hr, the inorganic salts were removed by filtration and the filtrate was washed with water to destroy excess phosgene. Concentration (after drying) in vacuo yielded 96.85 g of oily residue. Trituration of the residue with isopropyl ether yielded 42 g of crude tan-gray product. A sample for analysis was recrystallized from isopropyl ether, m.p. 87°-88° C.

Workup

  1. stirringAfter stirring for 5 hr
  2. customthe inorganic salts were removed by filtration
  3. washthe filtrate was washed with water
  4. customto destroy excess phosgene
  5. concentrationConcentration (after drying) in vacuo

Sources & evidence

ORD record
ord-391e650676be460882601a52e11da07c
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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