Triphosgene → p-(Tetradecyloxy)phenyl isocyanate

HRID 1461918Notes

Reaction equation

HRID 1461918 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH2:13]([O:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(Cl)Cl>[CH2:13]([O:27][C:28]1[CH:34]=[CH:33][C:31]([N:32]=[C:2]=[O:4])=[CH:30][CH:29]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 191002p-(n-Tetradecyloxy)phenylamine

Product 1

HCID 11724283p-(Tetradecyloxy)phenyl isocyanate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 8.74 g of triphosgene in 125 ml of methylene chloride cooled to 0° C. is added dropwise a solution of p-(tetradecyloxy)aniline, 7.95 g of 125 ml of methylene chloride over 30 minutes. Stirring at ambient temperature is continued for 4 hours. The solvent is evaporated and the residue stirred with ether and filtered. The cake is washed with additional ether and the combined filtrates evaporated to give the desired product as an oil.

Workup

  1. customThe solvent is evaporated
  2. stirringthe residue stirred with ether
  3. filtrationfiltered
  4. washThe cake is washed with additional ether
  5. customthe combined filtrates evaporated

Sources & evidence

ORD record
ord-d97234e6bd784ba9822fddd79537fc57
Source dataset
uspto-grants-1991_12
Patent number
US05077409

Reaction notes

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