Hydrochloric Acid → HCID 86688235, compound

HRID 2176724Notes

Reaction equation

HRID 2176724 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([O:14]C)=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].C(N(CC)CC)C.[C:23](Cl)(=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[OH-].[K+].Cl>O1CCCC1.O.CO>[C:23]([NH:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8])(=[O:39])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 66831Dimethyl 5-aminoisophthalate

Product 1

HCID 86688235HCID 86688235, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dimethyl 5-aminoisophthalate (Aldrich, 3.28 g, 15.7 mmol) and triethyl amine (3.4 mL, 24.7 mmol) were dissolved in dry tetrahydrofuran (90 mL) under inert atmosphere and cooled to 0° C. for at least 30 min. A solution of palmitoyl chloride (5 mL, 16.5 mmol) in THF (25 mL) was then added slowly, dropwise. The reaction was then allowed to warm slowly to room temperature and stirred for at least 1 h before deionized water (10 mL) was added and the tetrahydrofuran was removed by rotary evaporation. The crude residue was then suspended in deionized water (50 mL), filtered, washed with deionized water, and dried to give a white solid. The crude solid was then dissolved in refluxing methanol (200 mL). Potassium hydroxide (˜85%, 5.76 g, 0.102 mol) and deionized water (50 mL) were then added. After 1 h, the reaction was cooled to room temperature to give a cloudy white suspension. 5M HCl (25 mL) was added until the pH of the slurry was acidic, and the solid was filtered, washed with deionized water, and dried in vacuo to give a white solid (6.45 g, 98%). The product was identified by 1H and 13C NMR spectroscopy and ESI-MS and was of satisfactory purity. The product was believed to be of the formula

Workup

  1. temperatureto warm slowly to room temperature
  2. additionwas added
  3. customthe tetrahydrofuran was removed by rotary evaporation
  4. filtrationfiltered
  5. washwashed with deionized water
  6. customdried
  7. customto give a white solid
  8. dissolutionThe crude solid was then dissolved
  9. temperaturethe reaction was cooled to room temperature
  10. customto give a cloudy white suspension
  11. filtrationthe solid was filtered
  12. washwashed with deionized water
  13. customdried in vacuo

Sources & evidence

ORD record
ord-c167e86d0ea942248fd90d3a628523c8
Source dataset
uspto-grants-2015_06
Patent number
US09067878B2

Reaction notes

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