Triethylamine → CB 3034

HRID 1458706Notes

Reaction equation

HRID 1458706 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]C(O)=O)=[CH:10][CH:9]=1)[CH2:5][CH2:6][Cl:7].C([N:21](CC)CC)C.ClC(OCC)=O.[N-]=[N+]=[N-].[Na+]>CC(C)=O.O>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH2:21])=[CH:10][CH:9]=1)[CH2:5][CH2:6][Cl:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 23198NorchlorambucilHCID 33557Sodium Azide

Product 1

HCID 151580CB 3034Yield 83.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

3-[4-[N,N-Bis(2-chloroethyl)amino]phenyl]propionic acid (0.20 g; 0.69 mmol) was suspended in 1 ml of acetone and the resulting mixture was stirred under a nitrogen gas atmosphere and ice-cooling. Triethylamine (115 μl; 0.82 mmol; 1.2 equivalents) and ethyl chloroformate (79 μl; 0.82 mmol; 1.2 equivalents) were added successively. Fifteen minutes later, a solution of 90 mg (1.38 mmol; 2.0 equivalents) of sodium azide in 1 ml of water was added dropwise. The resulting mixture was stirred, as was, for 30 minutes, to which ice was added to terminate the reaction. The thus-obtained mixture was extracted three times with 15 ml portions of benzene. The benzene layers were combined, dried over sodium sulfate and then heated under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was added with 7.5 ml of 8N hydrochloric acid, followed by heating for 15 minutes at 100° C. The resulting mixture was concentrated under reduced pressure and the residue was diluted with water. The thus-obtained mixture was adjusted to pH 12 with concentrated aqueous ammonia, followed by extraction with ethyl acetate. The extract was dried and concentrated, whereby 0.15 g of the title compound was obtained as a brown oil. This reaction product was provided for use in the next reaction without purification.

Workup

  1. temperatureice-cooling
  2. stirringThe resulting mixture was stirred
  3. additionwas added
  4. customto terminate
  5. customthe reaction
  6. extractionThe thus-obtained mixture was extracted three times with 15 ml portions of benzene
  7. dry with materialdried over sodium sulfate
  8. temperatureheated
  9. temperatureunder reflux for 1 hour
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. additionThe residue was added with 7.5 ml of 8N hydrochloric acid
  12. concentrationThe resulting mixture was concentrated under reduced pressure
  13. additionthe residue was diluted with water
  14. extractionfollowed by extraction with ethyl acetate
  15. customThe extract was dried
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-187651ad67d045b5aba414fe088e7583
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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