Ammonia → (E,E)-3,7,11,15-tetramethyl-6,10,14-hexadecatrienamide

HRID 1263233Notes

Reaction equation

HRID 1263233 reaction equation
[NH3:1].[CH3:2][CH:3]([CH2:8][CH2:9]/[CH:10]=[C:11](\[CH3:23])/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH2:4][C:5](Cl)=[O:6]>O1CCCC1>[CH3:2][CH:3]([CH2:8][CH2:9]/[CH:10]=[C:11](\[CH3:23])/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH2:4][C:5]([NH2:1])=[O:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15589938(E,E)-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoic acid chloride

Product 1

HCID 15589939(E,E)-3,7,11,15-tetramethyl-6,10,14-hexadecatrienamideYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 100 ml of a tetrahydrofuran solution containing 1 g of ammonia, 9.5 g of the compound obtained in step (d) above was added dropwise at 0° to 5° C., and the mixture was stirred at room temperature for 30 minutes. The liquid reaction mixture was extracted with n-hexane, and the extract was washed with water and dried. The solvent was removed by distillation and the obtained oily substance was purified by column chromatography using silica gel to obtain 5.6 g of the intended compound in the form of an oil.

Workup

  1. additionabove was added dropwise at 0° to 5° C.
  2. customThe liquid reaction mixture
  3. extractionwas extracted with n-hexane
  4. washthe extract was washed with water
  5. customdried
  6. customThe solvent was removed by distillation
  7. customthe obtained oily substance was purified by column chromatography

Sources & evidence

ORD record
ord-5b4b6cb4c8684813989a2b9008544aeb
Source dataset
uspto-grants-1984_06
Patent number
US04456603

Reaction notes

Loading…