Triethylamine → p-(Tetradecyloxy)phenyl isocyanate

HRID 484597Notes

Reaction equation

HRID 484597 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(N(CC)CC)C.CN(C1C=CC=CN=1)C>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

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 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 triethylamine and 239.93 mg of dimethylaminopyridine in 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-9a79294db7044e9f8d0b2f8199af1d55
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

Loading…