Cesium carbonate → HCID 86722510, compound

HRID 526292Notes

Reaction equation

HRID 526292 reaction equation
Cl.[NH2:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[I:20][CH:21](I)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(#N)C>[NH2:2][C:3]([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][I:20])([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)HCID 543227511,1-Diiodohexadecane

Product 1

HCID 86722510HCID 86722510, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diethyl 2-aminomalonate hydrochloride (2.116 g, 10.0 mmol) and caesiumcarbonate (7.100 g, 21.8 mmol, 2.2 eq.) were suspended in acetonitrile (50 mL) and stirred at r.t. for 15 min. Then diiodohexadecane 28 (5.017 g, 10.5 mmol, 1.1 eq.) was added and the mixture was refluxed for 6 h. After cooling to r.t. and partial evaporation of the solvent, the residue was purified by column chromatography (silica gel, 16×4 cm, cyclohexane/ethyl acetate, 2:1) to give the product as a yellowish oil. Yield: 3.097 g (56%).

Workup

  1. temperaturethe mixture was refluxed for 6 h
  2. temperatureAfter cooling to r.t.
  3. custompartial evaporation of the solvent
  4. customthe residue was purified by column chromatography (silica gel, 16×4 cm, cyclohexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-81f5cb160f454caf97e52b620975888d
Source dataset
uspto-grants-2016_05
Patent number
US09345791B2

Reaction notes

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