1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66637839, compound

HRID 1644568Notes

Reaction equation

HRID 1644568 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-:7])=O)[CH:3]=1.[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH2:18].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:13][O:12][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([NH:18][CH2:17][CH:16]([O:19][CH3:20])[O:15][CH3:14])=[O:7])[CH:3]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 69512791,3-Benzenedicarboxylic acid, monomethyl ester

Product 1

HCID 66637839HCID 66637839, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Mono-methyl isophthalate (1 g, 5.55 mmol), amino acetaldehyde dimethyl acetal (569 μL, 5.28 mmol) and EDCI (1.52 g, 7.92 mmol) were dissolved in 55 mL DCM, followed by the addition of DIPEA (1.84 mL, 10.56 mmol). The reaction was allowed to stir at room temperature for 2 hours. It was then taken up in 50 mL of DCM, washed with saturated NaHCO3 solution (100 mL), and brine (100 mL). The organic layer was dried over MgSO4, filtered and concentrated to afford the crude product (1.48 g) as a clear oil which was used in the next step without further purification.

Workup

  1. washwashed with saturated NaHCO3 solution (100 mL), and brine (100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9a70b708afb9403695466ea9609bd7b3
Source dataset
uspto-grants-2012_02
Patent number
US08124627B2

Reaction notes

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