Triethylamine → 1-(3-Phenyl-2-propenoyl)-1H-benzotriazo&

HRID 533493Notes

Reaction equation

HRID 533493 reaction equation
[C:1]([OH:11])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CS([N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1)(=O)=O.C(N(CC)CC)C>O1CCCC1.C(#N)C>[N:16]1([C:1](=[O:11])/[CH:2]=[CH:3]/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 444539Cinnamic Acid2×HCID 7920441-(Methylsulfonyl)-1H-benzotriazole

Product 1

HCID 53382481-(3-Phenyl-2-propenoyl)-1H-benzotriazo&

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.42 g (0.01 mol) of trans-cinnamic acid (compound of formula IV) and 1.97 g (0.01 mol) of 1-(methylsulfonyl)benzotriazole are stirred at room temperature in 50 ml of tetrahydrofuran, followed by dropwise addition of 0.014 mol of triethylamine. The solution is then refluxed for 24 hours, and then evaporated under reduced pressure. The residue is taken up in 60 ml of water and extracted with 70 ml of ethyl acetate. The organic phase is dried, filtered and then concentrated under vacuum. The powder obtained is taken up in 50 ml of acetonitrile and filtered off by suction.

Workup

  1. temperatureThe solution is then refluxed for 24 hours
  2. customevaporated under reduced pressure
  3. extractionextracted with 70 ml of ethyl acetate
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe powder obtained
  8. filtrationfiltered off by suction

Sources & evidence

ORD record
ord-a3d2da41a7754e659006f4947e935aaf
Source dataset
uspto-grants-2014_10
Patent number
US08853276B2

Reaction notes

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