Triethylamine → HCID 14054112, compound

HRID 2072671Notes

Reaction equation

HRID 2072671 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7]([OH:9])=O.S(Cl)(Cl)=O.C(N(CC)CC)C.[CH3:21][C:22]1([CH3:33])[C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([NH2:31])[C:25]=2[CH:24]([CH3:32])[CH2:23]1>C(OCC)(=O)C>[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7]([NH:31][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:25]=1[CH:24]([CH3:32])[CH2:23][C:22]2([CH3:33])[CH3:21])=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 2447562-Methyl-3-furoic acidHCID 112175411,1,3-Trimethylindan-4-amine

Product 1

HCID 14054112HCID 14054112, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.5 g (11.9 mmols) of 2-methyl-3-furan carboxylic acid with 3 ml of thionyl chloride was refluxed for 1 hour. The reaction solution was distilled under reduced pressure to remove excess thionyl chloride. The obtained residue was cooled and 20 ml of ethyl acetate, 2 g (19.8 mmols) of triethylamine, and 1.8 g (10.3 mmols) of 1,1,3-trimethylindane-4-amine were added thereto. The resultant mixture was stirred at room temperature for 2 hours. The reaction solution was sequentially washed with water and brine. The organic layer consequently separated was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was purified by being recrystallized with ethyl acetate/n-hexane, to obtain 1.8 g of white crystals (Compound No. 17 shown in Table 6). The yield was 65%.

Workup

  1. temperaturewas refluxed for 1 hour
  2. distillationThe reaction solution was distilled under reduced pressure
  3. customto remove excess thionyl chloride
  4. temperatureThe obtained residue was cooled
  5. washThe reaction solution was sequentially washed with water and brine
  6. customThe organic layer consequently separated
  7. dry with materialwas dried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrated residue was purified
  10. customby being recrystallized with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e70c7a88468847a3b3494967c8d93d71
Source dataset
uspto-grants-1990_04
Patent number
US04914097

Reaction notes

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