2,5,8,11,14,17,20-Heptaoxadocosan-22-amine → HCID 178496251, compound

HRID 1527633Notes

Reaction equation

HRID 1527633 reaction equation
[N:1]1([C:6]([NH:8][C:9]2[NH:10][C:11]([CH3:16])=[CH:12][C:13](=[O:15])[N:14]=2)=[O:7])[CH:5]=[CH:4]N=C1.C[O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37]CN>C(OCC)(=O)C>[CH3:37][O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:4][CH2:5][NH:1][C:6]([NH:8][C:9]1[NH:10][C:11]([CH3:16])=[CH:12][C:13](=[O:15])[N:14]=1)=[O:7]

Participants

4

Reactant 2

HCID 187646512,5,8,11,14,17,20-Heptaoxadocosan-22-amineHCID 178429402HCID 178429402, compound

Product 1

HCID 178496251HCID 178496251, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4.38 g of 2-(1-imidazolylcarbonylamino)-6-methyl-4[1H]-pyrimidinone 1A (0.02 mol) in 200 ml of ethyl acetate were added 7.4 g of 2,5,8,11,14,17,20 heptaoxadocosan-22-amine (0.0218 mol). The reaction mixture was refluxed for 12 hours. The mixture was then allowed to return to room temperature, and was evaporated under reduced pressure. The residue was taken up in acetone (50 ml) and then filtered to remove the imidazole. The filtrate was evaporated under reduced pressure and then taken up again in 50 ml of acetone and filtered. The filtrate was evaporated under reduced pressure. 5.9 g of the expected product were thus obtained in the form of a pasty oil, in a yield of 60%. 1H and 13C NMR spectra compliant.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. customto return to room temperature
  3. customwas evaporated under reduced pressure
  4. filtrationfiltered
  5. customto remove the imidazole
  6. customThe filtrate was evaporated under reduced pressure
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c0c3b82db4ff4723bc9c7ea117dc9942
Source dataset
uspto-grants-2015_07
Patent number
US09089500B2

Reaction notes

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