Sodium Thiosulfate Pentahydrate → HCID 86612899, compound

HRID 2382517Notes

Reaction equation

HRID 2382517 reaction equation
[C:1]([O:5][C:6](=[O:29])[C:7]1[CH:12]=[CH:11][C:10]([N:13]=[N:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br)=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].O.O.O.O.O.[S:35]([O-])([O-])(=O)=S.[Na+].[Na+]>O.C(O)C>[C:1]([O:5][C:6](=[O:29])[C:7]1[CH:12]=[CH:11][C:10]([N:13]=[N:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][SH:35])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 61475Sodium Thiosulfate PentahydrateHCID 87857827HCID 87857827, compound

Product 1

HCID 86612899HCID 86612899, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-[4-(6-Mercapto-hexyloxy)-phenylazo]-benzoic acid t-butyl ester was synthesized by modifying a literature procedure [Material Science and Engineering, 1999, 8-9, 385-389; J. Phys. Chem., 1995, 99, 7102]. 0.41 g (0.9 mmol) of 4-[4-(6-bromo-hexyloxy)-phenyazo]-benzoic acid t-butyl ester and 0.25 mg (1.1 mmol) of sodium thiosulfate pentahydrate in 5 mL of water was dissolved in 18 mL of ethanol and refluxed for 3 hours. The mixture was stirred at room temperature for an additional hour. After cooling, the precipitate was filtered off using a fritted funnel. A fine orange solid (bunte salt) was obtained and was used without purification. 10 ml of chloroform and 10 mL of 1M HCl were added to the bunte salt. The reaction mixture was refluxed for 2 hours at 70° C. after which the orange organic phase was extracted from the colorless aqueous layer. The organic layers were further extracted with 10 mL of chloroform (3 times) and combined, washed with saturated NaHCO3 solution, distilled water, and then dried over MgSO4. The solvent was removed by roto-evaporation and the product (compound 1, FIG. 11) was further purified by recrystallization from an ethanol-water mixture. Drying under vacuum produced a fine orange powder (0.22 g, 60% yield) with the following characteristics: 1H NMR (CDCl3) δ 8.11 (d, J=9 Hz, 2H), 7.91 (dd, J=9 Hz, 4H), 7.14 (d, J=9 Hz, 2H), 4.08 (t, J=6 Hz, 2H), 2.48 (m, 2H), 1.85-1.41 (m, 17H), 1.32 (t, 1H). High-resolution mass spectroscopy (HR-MS) yielded a mass of 414.1988 compared to the value 414.1628 calculated for C23H30O3N2S.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-21a9e079c9474f898930ec4ebbc64c0b
Source dataset
uspto-grants-2012_09
Patent number
US08263192B2

Reaction notes

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