4-(Dibutylamino)benzaldehyde → HCID 46850905, compound

HRID 1807345Notes

Reaction equation

HRID 1807345 reaction equation
[Br-:1].[Br-].[CH3:3][C:4]1[CH:9]=[CH:8][N+:7]([CH2:10][CH2:11][CH2:12][N+:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:5]=1.[CH2:17]([N:21]([CH2:30][CH2:31][CH2:32][CH3:33])[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH3:20]>>[Br-:1].[Br-:1].[CH2:17]([N:21]([CH2:30][CH2:31][CH2:32][CH3:33])[C:22]1[CH:23]=[CH:24][C:25](/[CH:26]=[CH:3]/[C:4]2[CH:5]=[CH:6][N+:7]([CH2:10][CH2:11][CH2:12][N+:13]([CH3:14])([CH3:16])[CH3:15])=[CH:8][CH:9]=2)=[CH:28][CH:29]=1)[CH2:18][CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 6053914-(Dibutylamino)benzaldehydeHCID 16207064HCID 16207064, compound

Product 1

HCID 46850905HCID 46850905, compound

Procedure

To a dry vial was added the salt 6 (708 mg, 2 mmol), 4-dibutylaminobenzaldehyde (467 mg, 2 mmol) and the vial was purged with N2. Ethanol (10 ml) was added via syringe, followed by piperidine (1 ml). Within 5 minutes the color began changing to deep red. The mixture was stirred at room temperature for 12 hours, concentrated and the salt was precipitated with dry ether. Following solvent removal, the salt was again dissolved in EtOH (8 ml) and precipitated with ether. The resulting fluorophore was filtered under a nitrogen atmosphere and dried. Yield: 1.04 g (91%). MS (dual ESI+): 204.69186 (M+H+)2+ HRMS calc. 409.3457. H-NMR (DMSO-D6): 0.92 (t, J=12 Hz, 6H); 1.38 (m, 4H); 1.48 (m, 4H); 2.24 (m, 2H); 3.22l-3.35 (m, 11 H); 3.85 (t, J=9 Hz, 4H); 4.25 (t, J=12 Hz, 2H); 6.8 (d, J=8 Hz, 2H); 6.97 (s, 2H); 7.75 (d, J=8 Hz, 2H); 8.05 (d, J=6 Hz, 2H); 8.95 (d, J=6 Hz, 2H).

Workup

  1. customthe vial was purged with N2
  2. additionEthanol (10 ml) was added via syringe
  3. concentrationconcentrated
  4. customthe salt was precipitated with dry ether
  5. customFollowing solvent removal
  6. dissolutionthe salt was again dissolved in EtOH (8 ml)
  7. customprecipitated with ether
  8. filtrationThe resulting fluorophore was filtered under a nitrogen atmosphere
  9. customdried

Sources & evidence

ORD record
ord-deeba0d3b9194d52a8918563e1b98c18
Source dataset
uspto-grants-2013_01
Patent number
US08357350B2

Reaction notes

Loading…