1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Benzoic acid, 2-amino-4-(aminocarbonyl)-, methyl ester

HRID 1442577Notes

Reaction equation

HRID 1442577 reaction equation
[NH4+].O[N:3]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH2:24][C:25]1[CH:34]=[C:33]([C:35]([O-:37])=O)[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]>CN(C=O)C>[NH2:24][C:25]1[CH:34]=[C:33]([C:35]([NH2:3])=[O:37])[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21924002HCID 21924002, compoundHCID 220338091-Hydroxybenzotriazole, ammonium salt

Product 1

HCID 19064836Benzoic acid, 2-amino-4-(aminocarbonyl)-, methyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice cooling, 1-hydroxy-1H-benzotriazole ammonium salt (6.86 g, 45.1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.64 g, 45.1 mmol) were added to DMF solution (40 mL) of 1-methyl 2-aminoterephthalate (8.0 g, 41.0 mmol). The mixture was stirred at the same temperature for 1.5 hours and at room temperature for 30 minutes. After ice water was added to the reaction mixture, the precipitated crystals were taken by filtration and washed with water and diethyl ether. The filtrate was neutralized with sodium hydrogencarbonate, which was extracted 4 times with a tetrahydrofuran-ethyl acetate mixture. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was crystallized from water-ethyl acetate to give the title compound (7.32 g, 92%).

Workup

  1. filtrationthe precipitated crystals were taken by filtration
  2. washwashed with water and diethyl ether
  3. extractionwas extracted 4 times with a tetrahydrofuran-ethyl acetate mixture
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from water-ethyl acetate

Sources & evidence

ORD record
ord-eef6f95d1c034b939db760b8954146e4
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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