Phosgene → HCID 15053366, compound

HRID 2081381Notes

Reaction equation

HRID 2081381 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].[Br: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>[Br: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 15053363HCID 15053363, compound

Product 1

HCID 15053366HCID 15053366, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 18.8 g (0.192 mole) of phosgene in 100 ml of methylene chloride was cooled to 15° C. in a water bath, then treated with 26.5 g (0.192 mole) of potassium carbonate. After stirring for 30 min, 63 g (0.16 mole) of 3-(4-bromophenoxy)-1-diphenylmethylazetidine in 180 ml of methylene chloride was added dropwise and stirring continued for 18 hr. The reaction mixture was diluted with ice water to dissolve the inorganic salts, the aqueous portion was separated and the organic phase washed with 25 ml of ice water. After separation, the methylene chloride solution was dried with magnesium sulfate, then concentrated in vacuo to a viscous yellow oil. Trituration of the residue with 30/60 petroleum ether yielded a crystalline product, 76.9 g, which was recrystallized from isopropyl ether-ligroin (50-50) to yield 34.8 g (74.8%) of white granular crystals, m.p. 77°-78° C.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hr
  3. dissolutionto dissolve the inorganic salts
  4. customthe aqueous portion was separated
  5. washthe organic phase washed with 25 ml of ice water
  6. customAfter separation
  7. dry with materialthe methylene chloride solution was dried with magnesium sulfate
  8. concentrationconcentrated in vacuo to a viscous yellow oil
  9. customTrituration of the residue with 30/60 petroleum ether yielded a crystalline product, 76.9 g, which
  10. customwas recrystallized from isopropyl ether-ligroin (50-50)

Sources & evidence

ORD record
ord-faf4d792c8dd44caaa96c149af37ee7d
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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