Formic Acid → HCID 22490733, compound

HRID 2180863Notes

Reaction equation

HRID 2180863 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:23]([OH:25])=O.Cl.C(N=C=NCCCN(C)C)C.[C:38](OCC)(=[O:40])C.[CH3:44][OH:45]>CN(C)C1C=CN=CC=1.ClCCl.O>[CH:38]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH:23]=[O:25])=[CH:11][CH:10]=2)[C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH:44]=[O:45])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1)=[O:40]

Participants

9

Reactant 5

HCID 284Formic AcidHCID 887MethanolHCID 8857Ethyl AcetateHCID 68356Benzeneamine, 4,4',4''-methylidynetris- (9CI)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22490733HCID 22490733, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Tris(4-aminophenyl)methane (2.9 g), formic acid (4.6 g) and 4-dimethylaminopyridine (122 mg) were dissolved in dichloromethane (30 ml), after which 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (9.61 g) was added under a nitrogen atmosphere at 5° C., the temperature was raised to room temperature, and the mixture was stirred for 2 days. Ethyl acetate (100 ml) and water (50 ml) were added to the reaction mixture which was then vigorously shaken, and the organic layer was washed with saturated sodium bicarbonate water (20 ml), water (20 ml) and saturated aqueous sodium chloride (20 ml), dried over sodium sulfate, and concentrated to dryness. The residue was purified by silica gel column chromatography (Kieselgel 60, 240-400 mesh) and elution was performed with a mixed solvent of chloroform:methanol=90:10 to obtain 1.63 g of the title compound as a light brown powder (44% yield).

Workup

  1. stirringwas then vigorously shaken
  2. washthe organic layer was washed with saturated sodium bicarbonate water (20 ml), water (20 ml) and saturated aqueous sodium chloride (20 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by silica gel column chromatography (Kieselgel 60, 240-400 mesh) and elution

Sources & evidence

ORD record
ord-268da54416a24a9e9772d9cac32a3eae
Source dataset
uspto-grants-2005_05
Patent number
US06887890B2

Reaction notes

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