Triethylamine → HCID 19021796, compound

HRID 1614729Notes

Reaction equation

HRID 1614729 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([N:20]([CH2:23]C)CC)C.[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][C:26]=1C(O)=O>CN(C)C=O>[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][C:26]=1[N:20]=[C:23]=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96695Quinoxaline-2-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 19021796HCID 19021796, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diphenylphosphoryl azide (1.23 mL) was added to a solution of triethylamine (800 ul) and 2-quinoxaline carboxylic acid 1 g (5.74 mmol) stirring in 10 mL of dry dimethylformamide in an icewater cooling bath (2°). The reaction was stirred for 2.33 h during which time the reaction was allowed to warm to 25°. The reaction was poured into ice water and extracted three times with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and then concentrated in vacuo. The crude azide was dissolved in 15 mL of benzene and heated at reflux for 1.5 h. The solvent was removed in vacuo to provide the desired solid isocyanate. FT IR indicated a strong isocyanate absorption.

Workup

  1. temperaturecooling bath (2°)
  2. temperatureto warm to 25°
  3. extractionextracted three times with diethyl ether
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude azide was dissolved in 15 mL of benzene
  8. temperatureheated
  9. temperatureat reflux for 1.5 h
  10. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-851d51d2df9944dcba625a2e6f2c017a
Source dataset
uspto-grants-1993_03
Patent number
US05198560

Reaction notes

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