Acetone → HCID 178460162, compound

HRID 918937Notes

Reaction equation

HRID 918937 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH2:16])=[NH:15].CC(C)=O.O.[CH3:22][C:23]1([CH3:31])[C:27](=[O:28])[O:26][C:25]([CH:29]=[CH2:30])=[N:24]1.[OH-].[Na+:33]>>[S:1]([O-:5])([O-:4])(=[O:3])=[O:2].[Na+:33].[C:25]([NH:24][C:23]([CH3:31])([CH3:22])[C:27]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH2:16])=[NH2+:15])=[O:28])(=[O:26])[CH:29]=[CH2:30]

Participants

6

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 98127942-Ethenyl-4,4-dimethyl-1,3-oxazol-5(4H)-oneHCID 178512816HCID 178512816, compound2×

Product 1

HCID 178460162HCID 178460162, compound

Conditions

Temperature
10 °C

Procedure

Aminohexylguanidine sulfate (32.4 g, 127 mmol) was dissolved in 120 mL of aqueous 1.00 N NaOH. Acetone (60 mL) was then added and the stirred mixture was cooled to about 10° C. in a cold water bath. An additional 60 mL of H2O was added to keep the aminohexylguanidine sulfate in solution. 4,4-dimethyl-2-vinyl-1,3-oxazol-5(4H)-one (17.6 g, 137 mmol) was then added to the reaction mixture, via an addition funnel, over a period of 10 min. After stirring an additional 60 min, the reaction mixture was placed on a rotary evaporator at ambient temperature. After pulling off most of the acetone, the reaction mixture was transferred to a separatory funnel and washed with ethyl acetate (2×75 mL) and methylene chloride (2×25 mL). The remaining aqueous solution was brought to pH 7 by addition of dilute sulfuric acid and then placed on a rotary evaporator at ambient temperature to draw off any remaining volatiles. Lyophilization yielded the title compound (49 g) as a white powder 1H NMR (500 MHz, D2O) δ 6.37 (m, 1H), 6.25 (m, 1H), 5.84 (m, 1H), 3.26-3.24 (m, 4H), 1.68-1.38 (m, 14H). This monomer (0.71 grams), MBA (0.07 grams), PEG400MA (0.28 grams), and photoinitiator (31.2 μL of the photoinitiator solution of Example 14) were dissolved in enough methanol to provide 5 grams of coating solution. Primed membranes were coated, grafted, washed and dried as described in Example 1. Static and dynamic capacities for the grafted membrane were 110 and 71 mg/mL, respectively.

Workup

  1. customthe reaction mixture was placed on a rotary evaporator at ambient temperature
  2. customthe reaction mixture was transferred to a separatory funnel
  3. washwashed with ethyl acetate (2×75 mL) and methylene chloride (2×25 mL)
  4. additionThe remaining aqueous solution was brought to pH 7 by addition of dilute sulfuric acid
  5. customplaced on a rotary evaporator at ambient temperature

Sources & evidence

ORD record
ord-a02def364d6d4787ad75309088abd11d
Source dataset
uspto-grants-2016_03
Patent number
US09272246B2

Reaction notes

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