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Triethylamine → p-(Tetradecyloxy)phenyl isocyanate

HRID 483566
Notes
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Reaction equation

HRID 483566 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344Dichloromethane
Solvent
2×

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-c66b0fbf53db440681306edae315bba8
Source dataset
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05225425

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes