Sodium Thiosulfate Pentahydrate → 2,6-Diamino-5-iodo-nicotinic acid ethyl ester

HRID 2080007Notes

Reaction equation

HRID 2080007 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[N:7][C:6]=1[NH2:12])[CH3:2].[I:14]N1C(=O)CCC1=O.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([I:14])[C:8]([NH2:11])=[N:7][C:6]=1[NH2:12])[CH3:2]

Participants

5

Reactant 3

HCID 61475Sodium Thiosulfate PentahydrateHCID 120273N-IodosuccinimideHCID 58784252Ethyl 2,6-diaminonicotinate

Product 1

HCID 583880482,6-Diamino-5-iodo-nicotinic acid ethyl esterYield 35.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-diamino-nicotinic acid ethyl ester described in Preparation Example A-14 (1.4 g, 7.7 mmol) in N,N-dimethylformamide (15 mL) was added N-iodosuccinimide (2.09 g, 9.3 mmol), and the solution was stirred for 1 hour at room temperature. The reaction mixture was poured into an aqueous solution of saturated sodium thiosulfate pentahydrate, and the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) and the title compound (0.84 g, 2.7 mmol, 35.5%) was obtained.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-0b4d041727fb458b8adc4c865a0347cc
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…