Cyanuric acid → 6-Bromohexyl isocyanuric acid

HRID 718744Notes

Reaction equation

HRID 718744 reaction equation
S[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].N1C(=O)NC(=O)NC1=O.C([O-])([O-])=O.[K+].[K+].[Br:32]C(Br)CCCCC>CS(C)=O>[Br:32][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

6

Reactant 4

HCID 7956Cyanuric acidHCID 11430Potassium CarbonateHCID 118068541,1-DibromohexaneHCID 86659552Mercaptohexyl Isocyanuric Acid

Product 1

HCID 687551686-Bromohexyl isocyanuric acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A scheme for the synthesis of Mercaptohexyl Isocyanuric Acid (MH-ICA) is shown in FIG. 10A. 6-Bromohexyl isocyanuric acid was synthesized using methods and materials known in the art (see, e.g. Berl et al., Chem. Eur. J. 2000, 6, 1938-1946; and Hoeben et al., Org. Biomol. Chem. 2006, 4, 4460-4462). Briefly, 1-2 Cyanuric acid (6.2 g, 48 mmol) and ground K2CO3 (1.66 g, 12.0 mmol) were dissolved in DMSO (200 mL). After the mixture was stirred for 30 min, dibromohexane (2.98 g, 12.0 mmol, 0.25 equiv.) was added and was heated to 60° C. for 16 h. Upon cooling down the reaction to room temperature, the mixture solution was partitioned between diethyl ether and saturated KHSO4. The organic fraction was collected and the solvent was removed by rotary evaporator. Recrystallization of the residue from hexane yielded 6-bromohexyl isocyanuric acid which was extensively rinsed with hexane. The product (450 mg) was obtained in high purity. 1H NMR (500 MHz, DMSO-d6) δ: 11.38 (s, 2H), 3.62 (t, 2H), 3.52 (t, 2H), 1.78 (m, 2H), 1.50 (m, 2H), 1.38 (m, 2H), 1.27 (m, 2H) ppm; 13C NMR (125 MHz, DMSO-d6) δ: 149.85, 148.64, 40.28, 35.09, 32.12, 27.21, 27.15, 25.22 ppm. ESI-MS (M+): 293.98 (calculated 293.13).

Workup

  1. custom6-Bromohexyl isocyanuric acid was synthesized
  2. temperatureUpon cooling down
  3. customthe reaction to room temperature
  4. customthe mixture solution was partitioned between diethyl ether and saturated KHSO4
  5. customThe organic fraction was collected
  6. customthe solvent was removed by rotary evaporator
  7. customRecrystallization of the residue from hexane

Sources & evidence

ORD record
ord-cf6ff309f1164aeeb6df1c9d7a31b309
Source dataset
uspto-grants-2015_11
Patent number
US09194851B2

Reaction notes

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