Sodium Hydroxide → Mercaptohexyl Isocyanuric Acid

HRID 718745Notes

Reaction equation

HRID 718745 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:15](=[O:16])[NH:14][C:12](=[O:13])[NH:11][C:9]1=[O:10].NC(N)=[S:19].[OH-].[Na+]>C(O)C>[SH:19][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:15](=[O:16])[NH:14][C:12](=[O:13])[NH:11][C:9]1=[O:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 687551686-Bromohexyl isocyanuric acid

Product 1

HCID 86659552Mercaptohexyl Isocyanuric Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Mercaptohexyl isocyanuric acid (MH-ICA) was synthesized using methods and materials known in the art (see, e.g. Jogireddy et al., J. Synlett 2008, 1219-1221). Briefly, a solution of 6-bromohexyl isocyanuric acid (224 mg, 0.77 mmol) and thiourea (65 mg, 0.853 mmol) in ethanol (40 mL) was degassed (freeze, pump, thaw) thrice, and refluxed under an atmosphere of Ar for 24 h. After cooling down to room temperature, 2 mL NaOH (5 M) aqueous solution was added. The reaction solution was again degassed (freeze, pump, thaw) thrice and slowly heated to reflux. After refluxing for 24 h under Ar atmosphere and cooling down to room temperature, the mixture solution was acidified with 1 mL HCl (2 M) aqueous solution. The precipitate was filtered and extensively washed with deionized H2O to give the pure product, 6-mercaptohexyl isocyanuric acid (MH-ICA) in a yield of 85% (210 mg). 1H NMR (500 MHz, DMSO-d6) δ: 11.38 (s, 1H), 3.61 (t, 2H), 2.68 (s, 2H), 1.60 (m, 2H), 1.50 (m, 2H), 1.35 (m, 2H), 1.26 (m, 2H) ppm; 13C NMR (125 MHz, DMSO-d6) δ: 149.84, 148.64, 40.32, 37.71, 28.42, 27.41, 27.21, 25.70 ppm. ESI-MS (M+): 246.94 (calculated 246.09).

Workup

  1. custom6-Mercaptohexyl isocyanuric acid (MH-ICA) was synthesized
  2. temperaturerefluxed under an atmosphere of Ar for 24 h
  3. customThe reaction solution was again degassed (freeze, pump, thaw) thrice
  4. temperatureslowly heated to reflux
  5. temperatureAfter refluxing for 24 h under Ar atmosphere
  6. temperaturecooling down to room temperature
  7. filtrationThe precipitate was filtered
  8. washextensively washed with deionized H2O

Sources & evidence

ORD record
ord-2f40b9c7f9bc4adf95c39c7a840f1c45
Source dataset
uspto-grants-2015_11
Patent number
US09194851B2

Reaction notes

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