Toluene → HCID 15042230, compound

HRID 2371722Notes

Reaction equation

HRID 2371722 reaction equation
C(O)(=O)C(O)=O.C1(C(C2C=CC=CC=2)[N:14]2[CH2:17][CH:16]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[CH2:15]2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.[C:45]([Cl:48])(Cl)=[O:46]>O.C(Cl)Cl>[Cl:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][CH:16]1[CH2:17][N:14]([C:45]([Cl:48])=[O:46])[CH2:15]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 11430Potassium Carbonate2×HCID 85641428HCID 85641428, compound

Product 1

HCID 15042230HCID 15042230, compoundYield 146.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A slurry of 15.9 g (0.036 mole) of 1-(diphenylmethyl)-3-(3-chlorophenoxy)azetidine ethanedioate in 200 ml of water was treated with 10 g of potassium carbonate and 500 ml of toluene. This mixture was heated while stirring until the emulsion which had formed cleared and formed two clear phases. The toluene phase was separated, washed with hot water and concentrated in vacuo. The residue was dissolved in 50 ml of methlene chloride and added dropwise to a stirred mixture of 4 g (0.04 mole) of phosgene and 5.5 g (0.04 mole) of potassium carbonate in 50 ml of methylene chloride under nitrogen. After 2 hr the reaction mixture was treated with ice water to destroy the excess phosgene and dissolve the inorganic salts. The methylene chloride solution was separated, dried over magnesium sulfate and concentrated in vacuo to yield 13 g of residue. A sample was crystallized by cooling to -78° C. and was used to seed the residue which formed a semi-solid paste. Trituration of the paste with petroleum ether yielded 3.5 g (66.5%) of white powder upon filtration. Recrystallization from petroleum ether yielded 0.6 g of white crystalline product, mp 64°-65° C.

Workup

  1. temperatureThis mixture was heated
  2. customhad formed
  3. customformed two clear phases
  4. customThe toluene phase was separated
  5. washwashed with hot water
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in 50 ml of methlene chloride
  8. customto destroy the excess phosgene
  9. dissolutiondissolve the inorganic salts
  10. customThe methylene chloride solution was separated
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f00f66100444fecb44635ec20901bc5
Source dataset
uspto-grants-1992_03
Patent number
US05095014

Reaction notes

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