Ethyl chloroformate → (2E)-3-[1-(Phenylmethyl)-1H-pyrrol-2-yl]-2-propenoyl azide

HRID 549308Notes

Reaction equation

HRID 549308 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:17]C(Cl)=O)[CH3:16].[N-:21]=[N+:22]=[N-:23].[Na+]>CC(C)=O.O>[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1/[CH:13]=[CH:16]/[C:15]([N:21]=[N+:22]=[N-:23])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 111269641-benzyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 86761314(2E)-3-[1-(Phenylmethyl)-1H-pyrrol-2-yl]-2-propenoyl azideYield 67.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 1-benzyl-1H-pyrrole-2-carbaldehyde (28.4 g, 0.125 mol) and TEA (13.5 mL, 0.187 mol) in acetone (300 mL) was added ethylchloroformate (17.9 mL, 0.87 mol) dropwise. The reaction was stirred for 1.5 h after which NaN3 (13 g, 0.200 mol) in H2O (100 mL) was added. After 2 h, the reaction was diluted with water and left overnight. The acetone was removed and the product was filtered off to afford 21.4 g of a light brown solid. This compound was taken to the next step.

Workup

  1. additionwas added
  2. waitleft overnight
  3. customThe acetone was removed
  4. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-230dfa7350b1454789d18e1fffdde8aa
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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