Sodium Iodide → HCID 68785877, compound

HRID 1957818Notes

Reaction equation

HRID 1957818 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+].P(O)([O-])([O-])=O.[Na+].[Na+].Cl[CH2:39][C:40]([O:42][CH3:43])=[O:41]>CC(C)=O>[CH3:43][O:42][C:40](=[O:41])[CH2:39][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]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 24203Sodium Phosphate, DibasicHCID 1548943Capsaicin

Product 1

HCID 68785877HCID 68785877, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of Capsaicin (17 g, 55.7 mmol), anhydrous K2CO3 (26 g, 188 mmol), sodium iodide (4.5 g, 30 mmol) and disodium phosphate (4.5 g, 32 mmol) in anhydrous acetone (425 ml) was added methyl chloroacetate (9 g, 83 mmol) and refluxed for 6 hours. Acetone was distilled off and water (150 ml) was added. Crude 10 was filtered, dried and recrystallised from toluene to give pure 10 (15 g, 71.4%) as a white power. The melting point was found to be 99.5-103.5° C. It was analyzed by HPLC and found to be 99.3% pure.

Workup

  1. temperaturerefluxed for 6 hours
  2. distillationAcetone was distilled off
  3. additionwater (150 ml) was added
  4. filtrationCrude 10 was filtered
  5. customdried
  6. customrecrystallised from toluene

Sources & evidence

ORD record
ord-2f089d9ef0244abfb409f40e00dcf65a
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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