Triethylamine → HCID 15232832, compound

HRID 1110223Notes

Reaction equation

HRID 1110223 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH2:11])[CH:10]=1)[C:5]([OH:7])=[O:6].C(N([CH2:17][CH3:18])CC)C.[C:19](Cl)(=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C(Cl)Cl.C1COCC1>[O:29]=[C:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([NH:11][C:19](=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:17][CH3:18])[CH:10]=1)[C:5]([OH:7])=[O:6])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 120623,5-Diaminobenzoic acidHCID 66982Decanoyl chloride

Product 1

HCID 15232832HCID 15232832, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5 g (0.033 mol) of 3,5-diaminobenzoic acid in 100 ml of methylene chloride, 50 ml of THF and 18 ml (0.13 mol) of triethylamine stirred at room temperature was added 17 ml (0.08 mol) of decanoyl chloride dropwise over 10 minutes. The reaction mixture was stirred for 18 hours, filtered and the filtrate was concentrated at reduced pressure. Water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure and the solid residue was recrystallized twice from methanol-water to give 8.6 g (57% yield, mp 208°-209°) of 3,5-bis[(1-oxodecyl)amino]benzoic acid.

Workup

  1. stirringThe reaction mixture was stirred for 18 hours
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated at reduced pressure
  4. additionWater was added to the residue
  5. extractionthe product was extracted with ethyl acetate
  6. extractionThe dried extract
  7. concentrationwas concentrated at reduced pressure
  8. customthe solid residue was recrystallized twice from methanol-water

Sources & evidence

ORD record
ord-58c55d9bc8974d7a9e45d80feff3f1d4
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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