Ninhydrin → Sodium 4-sulfophenylthiourea

HRID 2230756Notes

Reaction equation

HRID 2230756 reaction equation
O.[S:2]([C:6]1[CH:11]=[CH:10][C:9]([N:12]=[C:13]=[S:14])=[CH:8][CH:7]=1)([OH:5])(=[O:4])=[O:3].[Na:15].C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O.C[N:30](C)CC=C>O>[S:2]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]([NH2:30])=[S:14])=[CH:10][CH:11]=1)([OH:5])(=[O:3])=[O:4].[Na:15]

Participants

5

Reactant 3

HCID 10236NinhydrinHCID 75082N,N-DimethylallylamineHCID 86584462Sodium 4-sulfophenylisothiocyanate monohydrate

Product 1

HCID 86584461Sodium 4-sulfophenylthiourea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
53 °C

Procedure

Solid sodium 4-sulfophenylisothiocyanate monohydrate (2.55 g; 10 mmol) was added to a solution of poly-L-lysine (15-30K) (Sigma Chemical Company) (1.0 g) in a mixture of water (20 ml) and N,N-dimethyl-N-allylamine buffer (pH 9.5; 15 ml). The resulting mixture was heated under nitrogen at 53° C. for 3 hours, when a ninhydrin test was negative. The cooled mixture was filtered and the filtrate concentrated to give a grey solid residue. The solid residue was redissolved in water and passed through a column of Amberlite IR 120(Na) and then concentrated. The crude product was purified by gel filtration (Sephadex LH20; water) and freeze dried to give sodium 4-sulfophenylthiourea terminated poly-L-lysine BRI2995 as a white fluffy solid (1.25 g).

Workup

  1. filtrationThe cooled mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customto give a grey solid residue
  4. concentrationconcentrated
  5. filtrationThe crude product was purified by gel filtration (Sephadex LH20; water)
  6. customfreeze dried

Sources & evidence

ORD record
ord-fd0d70003bdb48b28300582026269c06
Source dataset
uspto-grants-2002_07
Patent number
US06426067B1

Reaction notes

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