Benzaldehyde → HCID 15219579, compound

HRID 2185576Notes

Reaction equation

HRID 2185576 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:9].[CH3:10][C:11]1[CH:16]=[CH:15][N+:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=1>C(O)C>[I-:9].[CH2:13]([N:14]([C:5]1[CH:6]=[CH:7][C:2](/[CH:1]=[CH:10]/[C:11]2[CH:16]=[CH:15][N+:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=2)=[CH:3][CH:4]=1)[CH2:17][CH2:18][OH:19])[CH3:12]

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 15219576HCID 15219576, compound

Product 1

HCID 15219579HCID 15219579, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure of Example 6, equimolar amounts of 4-N-ethyl-N-hydroxyethylamino)benzaldehyde, prepared according to Example 2, and 4-methyl-N-(2-hydroxyethyl)pyridinium iodide, prepared according to Example 4, were reacted in ethanol at reflux, overnight. Upon cooling, dye3 precipitated as a red solid and was collected by filtration, washed, and dried. Yield: 67%. 1H-NMR (DMSO)-d6): δ 1.0 (t, 3H), 3.3 (q, 2H), 3.40 (q, 2H), 3.50 (t, 2H), 3.80 (q, 2H), 4.40 (t, 2H), 4.70 (t, 1H), 5.2 (t, 1H), 6.7 (d, 2H), 7.1 (d, 1H), 7.80 (d, 2H), 7.90 (d, 1H), 8.10 (d, 2H), 8.70 (d, 2H) ppm. The elements analy. calcd. for C19H25IN2O2: C, 51.8; H, 5.7; N, 6.4; Found: C, 51.5; H, 5.7; N, 7.1. Td 270° C.

Workup

  1. customprepared
  2. customprepared
  3. temperatureat reflux, overnight
  4. temperatureUpon cooling
  5. customdye3 precipitated as a red solid
  6. filtrationwas collected by filtration
  7. washwashed
  8. customdried
  9. customTd 270° C.

Sources & evidence

ORD record
ord-85e354498d8c4d1d8f4dc75362de94c4
Source dataset
uspto-grants-2002_06
Patent number
US06402037B1

Reaction notes

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