Phosgene → HCID 15042235, compound

HRID 1886578Notes

Reaction equation

HRID 1886578 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].C1(C(C2C=CC=CC=2)[N:18]2[CH2:21][CH:20]([O:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=3)[CH2:19]2)C=CC=CC=1>C(Cl)Cl>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[Cl:29])[O:22][CH:20]1[CH2:19][N:18]([C:1]([Cl:4])=[O:2])[CH2:21]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 150422273-(3,4-Dichlorophenoxy)-1-(diphenylmethyl)azetidine

Product 1

HCID 15042235HCID 15042235, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 14 g (0.144 mole) of phosgene in 200 ml of methylene chloride was treated with 19.9 g (0.144 mole) of anhydrous potassium carbonate and stirred for 1 hr, then 45.9 g (0.12 mole) of 1-diphenylmethyl-3-(3,4-dichlorophenoxy)azetidine in 100 ml of methylene chloride was added dropwise and stirring was continued for 72 hr. The reaction mixture was filtered to remove the inorganic salts and then concentrated in vacuo to a pale yellow oil (67 g). Trituration of the residue with cyclohexane yielded a crude pale yellow solid (23.6 g). The filtrate was treated with ligroin and upon standing, an additional 13.3 g of tacky material was obtained. After several recrystallizations from cyclohexane to remove traces of diphenylmethyl chloride a portion was obtained as fine white crystals, in 70.1% yield, m.p. 96°-99° C.

Workup

  1. stirringstirring
  2. waitwas continued for 72 hr
  3. filtrationThe reaction mixture was filtered
  4. customto remove the inorganic salts
  5. concentrationconcentrated in vacuo to a pale yellow oil (67 g)
  6. customTrituration of the residue with cyclohexane yielded a crude pale yellow solid (23.6 g)

Sources & evidence

ORD record
ord-7888d10ac163484ca9894c80e7f97504
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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