Hydroquinone → 3-[(3-Acrylamidopropyl)dimethylammonio]propane-1-sulfonate

HRID 2188194Notes

Reaction equation

HRID 2188194 reaction equation
[C:1]([NH:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10])(=[O:4])[CH:2]=[CH2:3].C1(C=CC(O)=CC=1)O.[CH2:20]1[S:24](=[O:26])(=[O:25])[O:23][CH2:22][CH2:21]1>C(#N)C>[C:1]([NH:5][CH2:6][CH2:7][CH2:8][N+:9]([CH3:11])([CH3:10])[CH2:22][CH2:21][CH2:20][S:24]([O-:23])(=[O:26])=[O:25])(=[O:4])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 14264Propane sultoneHCID 77452N,N-Dimethylaminopropyl acrylamide

Product 1

HCID 111735023-[(3-Acrylamidopropyl)dimethylammonio]propane-1-sulfonateYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The solution of 6.2 g 3-acrylamidopropyldimethylamine (M=156.23 g/mol-39.7 mmol) and of 88 mg hydroquinone (M=110.11 mol/l-0.02 eq.) in 17 ml anhydrous acetonitrile is magnetically stirred at ambient temperature in an argon stream. The solution of 3.5 ml distilled propanesultone (M=122.14 g/mol-d=1.392-1 eq.) in 5 ml anhydrous acetonitrile is added drop by drop. A white precipitate appears. The suspension is stirred in an argon stream for 24 hours at ambient temperature. The precipitate is then filtered, washed with anhydrous acetonitrile, then with anhydrous acetone, and dried. 10.3 g 3-[(3-acrylamidopropyl)dimethylammonio]propanesulfonate (M=278.36 g/mol) are thus obtained. Yield: 93%. The purity of the product is controlled by elemental analysis: C: 47.27%; H: 7.88%; N: 10.41%; S: 11.55%, the percentages calculated from the empirical formula (C11H22N2O4S) being as follows: C, 47.46%, H: 7.97%, N: 10.06%; S, 11.52%.

Workup

  1. additionis added drop by drop
  2. filtrationThe precipitate is then filtered
  3. washwashed with anhydrous acetonitrile
  4. dry with materialwith anhydrous acetone, and dried

Sources & evidence

ORD record
ord-c3da65a216f749e6adcfa62bc2c5e075
Source dataset
uspto-grants-2002_06
Patent number
US06410671B1

Reaction notes

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