N,N-Dimethylallylamine → Sodium 3,6,8-trisulfonaphthylthiourea

HRID 2100223Notes

Reaction equation

HRID 2100223 reaction equation
[S:1]([C:5]1[CH:6]=[C:7]([N:23]=[C:24]=[S:25])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:10][C:9]=2[S:19]([OH:22])(=[O:21])=[O:20])([OH:4])(=[O:3])=[O:2].[Na:26].C[N:28](C)CC=C>O>[S:1]([C:5]1[CH:6]=[C:7]([NH:23][C:24]([NH2:28])=[S:25])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]([OH:18])(=[O:16])=[O:17])=[CH:10][C:9]=2[S:19]([OH:22])(=[O:21])=[O:20])([OH:4])(=[O:3])=[O:2].[Na:26]

Participants

4

Reactant 2

HCID 75082N,N-DimethylallylamineHCID 86588645Sodium 3,6,8-trisulfonaphthylisothiocyanate

Product 1

HCID 86588644Sodium 3,6,8-trisulfonaphthylthiourea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Solid sodium 3,6,8-trisulfonaphthylisothiocyanate (250 mg; 0.5 mmol) was added to a solution of PAMAM 4.0 (51 mg; 0.01 mmol) and N,N-dimethyl-N-allylamine buffer (pH 9.5; 1 ml) in water (2 ml) and the mixture heated under nitrogen at 53° for two hours and then cooled. The mixture was concentrated under reduced pressure to give an orange solid. The residual solid was dissolved in water (2 ml) and passed through a short column of Amberlite IR-120(Na). The filtrate was then concentrated and the residue purified by gel filtration (Sephadex LH20; water). The pure fractions were combined and freeze dried to give the sodium 3,6,8-trisulfonaphthylthiourea terminated PAMAM 4.0 dendrimer as an off-white solid (102 mg). 1H nmr (D2O): δ2.65; 3.02; 3.30; 3.66; 8.05; 8.42; 8.59; 8.67. 13C nmr (D2O): δ33.2; 38.7; 43.2; 43.7; 47.8; 54.0; 54.3; 56.7; 131.0; 131.3; 131.9; 135.9; 138.0; 139.6; 143.8; 144.1; 145.6; 176.2; 176.5; 186.0.

Workup

  1. temperaturethe mixture heated under nitrogen at 53° for two hours
  2. temperaturecooled
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto give an orange solid
  5. concentrationThe filtrate was then concentrated
  6. filtrationthe residue purified by gel filtration (Sephadex LH20; water)
  7. customfreeze dried

Sources & evidence

ORD record
ord-151fa62bfa8b410fabcfa42e843fcd00
Source dataset
uspto-grants-2009_08
Patent number
US07572459B2

Reaction notes

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