Diphosgene → HCID 15020210, compound

HRID 973449Notes

Reaction equation

HRID 973449 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:3]=1[NH2:4].ClC([O:14][C:15](Cl)(Cl)Cl)=O.[CH2:19]([C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(Cl)Cl>[CH2:19]([C:27]1[CH:28]=[CH:29][C:30]([NH:31][C:15]([NH:4][C:3]2[C:2]([Cl:1])=[CH:8][C:7]([Cl:9])=[CH:6][C:5]=2[Cl:10])=[O:14])=[CH:32][CH:33]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 124712,4,6-TrichloroanilineHCID 853464-Octylaniline

Product 1

HCID 15020210HCID 15020210, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 10 ml methylene chloride solution of 1.0 g (5.09 mmol) of 2,4,6-trichloroaniline was added dropwise over 2 minutes to a 10 ml methylene chloride solution of 0.6 ml (4.97 mmol) of trichloromethyl chloroformate cooled to 5°-6° C. After stirring at 5°-6° C. for 2 hours, the mixture was added with 1.04 g (5.06 mmol) of 4-octylaniline and then stirred at room temperature for 16 hours. The reaction mixture was extracted with chloroform, and washed with an aqueous saturated solution of sodium hydrogen carbonate and an aqueous saturated solution of sodium chloride, successively. The organic layer was dried over anhydrous magnesium sulfate. After the removal of the solvent under reduced pressure, the residue was recrystallized from a mixed solvent of n-heptane and chloroform to give 0.95 g (43% yield) of 1-(4-octylphenyl)-3-(2,4,6-trichlorophenyl)urea, the physical properties of which being shown in the following Table 3. The compounds No. 4 and No. 11 listed in Table 3 were similarly prepared as above.

Workup

  1. temperaturecooled to 5°-6° C
  2. stirringstirred at room temperature for 16 hours
  3. extractionThe reaction mixture was extracted with chloroform
  4. washwashed with an aqueous saturated solution of sodium hydrogen carbonate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customAfter the removal of the solvent under reduced pressure
  7. customthe residue was recrystallized from a mixed solvent of n-heptane and chloroform

Sources & evidence

ORD record
ord-580b36c31e524a06b73fdb7743d05a6d
Source dataset
uspto-grants-1991_11
Patent number
US05063247

Reaction notes

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