Cyanoacetic acid → HCID 18467182, compound

HRID 2229215Notes

Reaction equation

HRID 2229215 reaction equation
[CH3:1][N:2]([CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)CCO.[C:12]([CH2:14][C:15]([OH:17])=[O:16])#[N:13].[CH2:18]1CCC(N=C=NC2CCCCC2)C[CH2:19]1>C1COCC1>[CH2:18]([O:16][C:15](=[O:17])[CH:14]([C:12]#[N:13])[N:2]([CH3:1])[CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:19]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 11206033HCID 11206033, compound

Product 1

HCID 18467182HCID 18467182, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[Methyl(2-thienylmethyl)amino]ethanol (0.017 mol, 3 g) and cyanoacetic acid (0.017 mol, 1.5 g) were dissolved in 200 mL of THF and DCC (0.019 mol, 3.8 g) was added. After 3 h, the resulting solid was removed and the filtrate was concentrated. The residue was passed through a six-inch silica plug using ether as solvent to give 4.0 g of product. 1H NMR (300 MHz) CDCl3: 7.25 (d, 1H), 7.0-6.8 (m, 2H), 4.33 (t, 2H) 3.76 (s, 2H), 3.47 (s, 2H), 2.70 (t, 2H), 2.35 (s, 3H).

Workup

  1. customthe resulting solid was removed
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f9c23f9d875f459db903ebaf67b33e53
Source dataset
uspto-grants-2002_07
Patent number
US06420383B1

Reaction notes

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