Triethylamine → HCID 70023647, compound

HRID 1168629Notes

Reaction equation

HRID 1168629 reaction equation
Cl.[C:2](=[NH:10])([O:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH2:5][CH3:6].C(N(CC)CC)C.[Cl-].[C:19]([O:30][CH3:31])(=[O:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24]([O-])=[O:25])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[CH3:31][O:30][C:19](=[O:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:10]=[C:2]([O:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH2:5][CH3:6])=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12283341Ethyl pentanimidate hydrochlorideHCID 22493623Monomethyl terephthalate chloride

Product 1

HCID 70023647HCID 70023647, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of ethyl pentanimidate hydrochloride (9 g, 54 mmol) and triethyl amine (17 mL, 120 mmol) in toluene (110 mL) at 0° C. was added, over 20 minutes, a solution of terephthalic acid, monomethyl ester chloride (10.8 g, 54 mmol) in toluene (21 mL). After stirring at ambient temperature for 19 hours, the reaction was filtered and the solids were rinsed with toluene (200 mL). The combined filtrates were concentrated in vacuo. Flash chromatography (silica gel, CH2Cl2) of a portion of this material afforded the title compound (1.9 g, 47%).

Workup

  1. filtrationthe reaction was filtered
  2. washthe solids were rinsed with toluene (200 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-a88d7140726747968e3514b26db3eb8c
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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