Sodium Iodide → HCID 68787870, compound

HRID 638704Notes

Reaction equation

HRID 638704 reaction equation
[CH3:1][CH:2](/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:22])=[C:18]([O:20][CH3:21])[CH:19]=1)=[O:11])[CH3:3].C([O-])([O-])=O.[K+].[K+].[I-].[Na+].Cl[CH:32]([CH3:37])[C:33]([O:35][CH3:36])=[O:34]>CC(C)=O>[CH3:36][O:35][C:33](=[O:34])[CH:32]([O:22][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][NH:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH:4][CH:2]([CH3:1])[CH3:3])=[CH:19][C:18]=1[O:20][CH3:21])[CH3:37]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 28659Methyl 2-chloropropionateHCID 1548943Capsaicin

Product 1

HCID 68787870HCID 68787870, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of Capsaicin (2 g, 6.56 mmol), anhydrous K2CO3 (3 g, 22 mmol), and sodium iodide (2 g, 14.2 mmol) in anhydrous acetone (50 ml) was added methyl 2-chloropropionate (1.2 g, 10 mmol) and refluxed for 16 hours. Acetone was distilled off and water (15 ml) was added. Crude 11 was filtered, dried and recrystallised from a mixture of chloroform:hexane (1:5) to give pure 11 (0.8 g, 31.2%) as a white powder. The melting point was found to be 62.3-64° C.

Workup

  1. temperaturerefluxed for 16 hours
  2. distillationAcetone was distilled off
  3. additionwater (15 ml) was added
  4. filtrationCrude 11 was filtered
  5. customdried
  6. customrecrystallised from a mixture of chloroform:hexane (1:5)

Sources & evidence

ORD record
ord-2ec28ec814674cb7ac7982ffcd4e0251
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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