p-Toluenesulfonic acid → HCID 69292549, compound

HRID 2219789Notes

Reaction equation

HRID 2219789 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH2:12]([CH:14]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:15][O:16][C:17](=[O:21])[CH2:18][C:19]#[N:20])[CH3:13].OC(C)CNCC(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CN(C)C=O.O>[CH2:12]([CH:14]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:15][O:16][C:17](=[O:21])[C:18]([C:19]#[N:20])=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1)[CH3:13]

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8086DiisopropanolamineHCID 120884-Formylbenzoic acidHCID 963592-Ethylhexyl cyanoacetate

Product 1

HCID 69292549HCID 69292549, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A 250 ml three necked reaction flask, equipped with a reflux condenser combined with a water separator and an oil bath with a magnetic stirrer was charged with 3.8 g (25 mmol) of 4-carboxy-benzaldehyde (Fluka), 6.8 g (33 mmol) of cyanacetic-acid-2-ethyl-hexylester, 0.3 g of bis-(2-hydroxypropyl)-amine and 0.25 g of p-toluene-sulfonic acid in 80 ml of toluene and 20 ml of dimethylformamide. After 22 hours under reflux the reaction mixture was diluted with toluene and washed with aqueous NH4Cl and NaCl solutions, dried with Na2SO4 and concentrated to yield 6.2 g (74%) of whire crystals. M.p. 159-162° C. W(CH2C2) 305 nm (E=811).

Workup

  1. temperatureAfter 22 hours under reflux the reaction mixture
  2. washwashed with aqueous NH4Cl and NaCl solutions
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customto yield 6.2 g (74%) of whire crystals

Sources & evidence

ORD record
ord-95517ed9513a40df9bb876998062206a
Source dataset
uspto-grants-2008_08
Patent number
US07414138B2

Reaction notes

Loading…