Phosgene → HCID 15042229, compound

HRID 2371721Notes

Reaction equation

HRID 2371721 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:15]([O:16][CH:17]2[CH2:20][N:19](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:18]2)=[CH:14][CH:13]=1>C(Cl)Cl>[Cl:11][C:12]1[CH:35]=[CH:34][C:15]([O:16][CH:17]2[CH2:18][N:19]([C:1]([Cl:4])=[O:2])[CH2:20]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 5974941-Benzhydryl-3-(4-chlorophenoxy)azetane

Product 1

HCID 15042229HCID 15042229, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 32.34 g (0.33 mole) of phosgene in 200 ml of methylene chloride cooled with a tap water bath was treated with 45.5 g (0.33 mole) of potassium carbonate and stirred for 30 min. Then 105 g (0.3 mole) of 3-(4-chlorophenoxy)-1-(diphenylmethyl)azetidine in 600 ml of methylene chloride was added dropwise. After stirring for an additional 18 h, the reaction mixture was filtered to remove the inorganic salts then concentrated in vacuo to a oily residue, 127.7 g. A solid formed upon standing which was triturated with boiling petroleum ether 3 times to remove the diphenylmethyl chloride. The residue, 33 g of dark brown crystalline material, was mainly starting material. Upon standing a white crystalline material separated from the petroleum ether triturates (4.4 g, mp 78°-80° C., sent for elemental analysis). The triturates were concentrated in vacuo yielding 31 g of pale yellow tacky crystals. Trituration of these crystals with 2-propyl ether yielded 21.9 g (36%) of pale yellow crystalline product.

Workup

  1. stirringAfter stirring for an additional 18 h
  2. filtrationthe reaction mixture was filtered
  3. customto remove the inorganic salts
  4. concentrationthen concentrated in vacuo to a oily residue, 127.7 g
  5. customA solid formed
  6. customwas triturated with boiling petroleum ether 3 times
  7. customto remove the diphenylmethyl chloride
  8. customseparated from the petroleum ether
  9. concentrationThe triturates were concentrated in vacuo

Sources & evidence

ORD record
ord-06fb5b47671f4a19adc28c152e4a3ec1
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Reaction notes

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