Thiosulfate ion → HCID 58532315, compound

HRID 1404605Notes

Reaction equation

HRID 1404605 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[NH2:13]Cl.S([O-])([O-])(=O)=S.[Cl-].[NH4+]>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([NH2:13])[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 1084Thiosulfate ionHCID 24758Sodium hydrideHCID 25423MonochloramineHCID 25517Ammonium ChlorideHCID 242292566-Bromo-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 58532315HCID 58532315, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-Bromo-1H-pyrrolo[3,2-b]pyridine (1.9 g, 10 mmol) in 20 mL of DMF at 0° C. was added NaH (60% in oil, 0.49 g, 12 mmol) in three portions. The mixture was stirred at room temperature for 30 min. A solution of NH2Cl in Et2O (prepared according to the procedure described in J. Org. Chem. 2004, 1371: ˜0.15 M, 80 mL) was added at −20° C. The mixture was warmed up to room temperature for 15 min and was poured into a saturated solution of thiosulfate and ammonium chloride, and extracted with ethyl acetate. The organic layer was concentrated and the residue washed with small amount of ethyl acetate to give pink solid (1.3 g, 62% yield)

Workup

  1. addition2004, 1371: ˜0.15 M, 80 mL) was added at −20° C
  2. temperatureThe mixture was warmed up to room temperature for 15 min
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. washthe residue washed with small amount of ethyl acetate

Sources & evidence

ORD record
ord-adcb3176c40941ea9d08347cdd51b507
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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