Triethylamine → HCID 67065126, compound

HRID 2369460Notes

Reaction equation

HRID 2369460 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH2:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(N([CH2:18][CH3:19])CC)C.[CH2:20]([CH:30]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:31](Cl)=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[CH2:34]([CH:30]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:18][CH3:19])[C:31]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH:12][C:31](=[O:32])[CH:30]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:32])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7010431Methyl 3,5-diaminobenzoateHCID 539445462-Decyltetradecanoyl chloride

Product 1

HCID 67065126HCID 67065126, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 3,5-diaminobenzoate (260.8 mg, 1.9 mmol) is dissolved in dry tetrahydrofuran (5 mL) in a 100 mL vessel under an inert atmosphere. Triethylamine (0.7 mL, 4.99 mmol) is then added and the solution is cooled to 0° C. A solution of 2-decyltetradecanoyl chloride from Step I in dry tetrahydrofuran (10 mL) is then added slowly, dropwise. The reaction is then allowed to slowly warm to room temperature. After stirring overnight, the reaction is quenched with water and the tetrahydrofuran is removed by rotary evaporation. The crude product residue is then dissolved in diethyl ether (50 mL) and is washed with deionized water (20 mL). The ether layer is separated and concentrated to give methyl 3,5-bis(2′-decyltetradecanamido)benzoate as a pale pink solid (1.17 g).

Workup

  1. temperatureto slowly warm to room temperature
  2. customthe reaction is quenched with water
  3. customthe tetrahydrofuran is removed by rotary evaporation
  4. dissolutionThe crude product residue is then dissolved in diethyl ether (50 mL)
  5. washis washed with deionized water (20 mL)
  6. customThe ether layer is separated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-065c4535797944648e67e4e9163dfae9
Source dataset
uspto-grants-2014_04
Patent number
US08703988B2

Reaction notes

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