Triethylamine → HCID 19884929, compound

HRID 846196Notes

Reaction equation

HRID 846196 reaction equation
C([CH:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:5][CH2:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH3:18])=[CH:10][CH:9]=1)(O)=O.C([N:27]([CH2:30]C)CC)C.ClC(OCC)=[O:34].[N-]=[N+]=[N-].[Na+]>O.C1(C)C=CC=CC=1.CC(C)=O>[N:27]([CH:4]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:5][CH2:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH3:18])=[CH:10][CH:9]=1)=[C:30]=[O:34]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 19884920HCID 19884920, compound

Product 1

HCID 19884929HCID 19884929, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a 1 l. one-neck round bottom flask fitted with a nitrogen inlet tube and addition funnel was added 7.05 g (220 mmol) of 1-carboxy-1-phenyl-3-(4-methyl-1-naphthalenyloxy)propane and 400 ml of acetone. To the mixture was added 3.2 ml (22.9 mmol) of triethylamine and the resulting mixture was cooled to approximately 0° C. To the mixture was added 2.2 ml of ethyl chloroformate dropwise. The mixture was stirred 30 minutes at about 0° C. and 2.72 g (41.8 mmol) of sodium azide dissolved and a small amount of water was added dropwise. The mixture was stirred for about 60 minutes at about 0° C. and 200 ml of toluene was added. Water was added to the reaction mixture and the aqueous phase was separated and extracted twice with 200 ml of toluene. The organic extracts were combined, washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was heated on a steam bath for two hours to induce formation of the isocyanate. The mixture was concentrated under vacuum to provide 7.6 g of the title compound which was used directly in the following reaction.

Workup

  1. customone-neck round bottom flask fitted with a nitrogen inlet tube and addition funnel
  2. stirringThe mixture was stirred for about 60 minutes at about 0° C.
  3. customthe aqueous phase was separated
  4. extractionextracted twice with 200 ml of toluene
  5. washwashed with water
  6. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  7. customThe sodium sulfate was removed by filtration
  8. temperaturethe filtrate was heated on a steam bath for two hours
  9. concentrationThe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-369638042a8d483d94a3c51d0bdca090
Source dataset
uspto-grants-1992_08
Patent number
US05135947

Reaction notes

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