Ammonia → HCID 86741397, compound

HRID 1031624Notes

Reaction equation

HRID 1031624 reaction equation
C(OCC)C.[CH3:6][C:7]([CH:14]=[CH:15][CH:16]=[C:17]([CH3:29])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[CH:8][C:9](OCC)=[O:10].C(Cl)(=O)OCC.[NH3:36]>C(N(CC)CC)C>[CH3:6][C:7]([CH:14]=[CH:15][CH:16]=[C:17]([CH3:29])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[CH:8][C:9]([NH2:36])=[O:10]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 10928Ethyl chloroformateHCID 54362700HCID 54362700, compound

Product 1

HCID 86741397HCID 86741397, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In 20 ml. of diethyl ether was dissolved 3.0 g. of the above-obtained 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid. To this solution was added 1 g. of triethylamine, and further added 1.1 g. of ethyl chlorocarbonate under stirring at room temperature. After 10 minutes, gaseous ammonia was introduced into the solution. The reaction liquid was washed with three 10 ml. portions of water, dried over magnesium sulfate, and evaporated to remove the solvent. The residue was purified by alumina column chromatography and crystallized from a mixture of acetone and n-hexane (1:2). There was obtained 1.7 g. of the desired product as pale yellow crystals.

Workup

  1. additionTo this solution was added 1 g
  2. customThe reaction liquid
  3. washwas washed with three 10 ml
  4. dry with materialportions of water, dried over magnesium sulfate
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue was purified by alumina column chromatography
  8. customcrystallized from a mixture of acetone and n-hexane (1:2)
  9. customThere was obtained 1.7 g

Sources & evidence

ORD record
ord-175ceb6d5e4842b3a926de2fe4e502f6
Source dataset
uspto-grants-1990_09
Patent number
US04954525

Reaction notes

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