Cysteamine → HCID 67111967, compound

HRID 404527Notes

Reaction equation

HRID 404527 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH2:17][SH:18]>CCO>[NH2:15][CH2:16][CH2:17][S:18][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([S:18][CH2:17][CH2:16][NH2:15])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6058CysteamineHCID 425529956,6'-Dichloro-3,3'-bipyridine

Product 1

HCID 67111967HCID 67111967, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared as described by Constable et al.13 The same reaction was repeated using 6,6′-dichloro-3,3′-bipyridine (0.154 g, 0.684 mmol) in EtOH (150 mL) under reflux for 24 h to give a yellow oil. The crude product showed the presence of cysteamine (1H n.m.r.) and washing with water gave a clean product (1.3 g, 75%). Mass spectrum (ESI): m/z 153.9 [½ (M+2H)2+]; 307.2 (M+H)+. 1H n.m.r. (300 MHz, CDCl3): δ 1.5 (bs, 4H); 3.02 (t, J 6.4 Hz, 4H); 3.32 (t, J 6.4 Hz, 4H); 7.26 (dd, J 8.4, 0.6 Hz, 2H); 7.63 (dd, J 8.4, 2.4 Hz, 2H); 8.60 (d, J 2.4 Hz, 2H). 13C n.m.r. (75 MHz, CDCl3): δ 34.4; 42.1; 122.8; 129.4; 134.3; 147.7; 156.1. Spectra were consistent with literature data13.

Workup

  1. customas described by Constable et al.13 The same reaction
  2. temperatureunder reflux for 24 h
  3. customto give a yellow oil
  4. washwashing with water

Sources & evidence

ORD record
ord-63a5161a5d2045f8b65fa770ecb50bd2
Source dataset
uspto-grants-2014_06
Patent number
US08748582B2

Reaction notes

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