Triethylamine → HCID 86739939, compound

HRID 371231Notes

Reaction equation

HRID 371231 reaction equation
[N:1]([CH2:4][C:5]([OH:7])=O)=[N+:2]=[N-:3].C(N(CC)CC)C.[C:15]1([CH:21]=[CH:22][CH:23]=[N:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[N:1]([C@H:4]1[C@@H:23]([CH:22]=[CH:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:24]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[C:5]1=[O:7])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 155605Azidoacetic acidHCID 291021HCID 291021, compound

Product 1

HCID 86739939HCID 86739939, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-Azidoacetic acid (24.26 g) is dissolved in 100 ml of methylene chloride and cooled in an ice bath. To this solution is added 48.57 g of triethylamine and 14.24 g of N-(3-phenyl-2-propenylidene)-4-methoxyaniline dissolved in 250 ml of methylene chloride. To the resulting solution is added 50.41 g of trifluoroacetic anhydride dropwise over a one hour period. After stirring for one hour in an ice bath, the mixture is warmed to room temperature and stirred for about 16 hours. The mixture is then diluted with 250 ml of methylene chloride and washed with water (750 ml), 5% sodium bicarbonate solution (two 750 ml portions), and 1N HCl solution (750 ml). The organic layer is dried over anhydrous sodium sulfate and stripped of solvent to give a solid. The crude product is recrystallized from ethyl acetate to give 11.39 g of the title compound as a solid.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred for about 16 hours
  3. washwashed with water (750 ml), 5% sodium bicarbonate solution (two 750 ml portions), and 1N HCl solution (750 ml)
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. customto give a solid
  6. customThe crude product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8c4449c36d084615aa66ebaa43fc2f6e
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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