Sodium Thiosulfate → HCID 68609793, compound

HRID 2406735Notes

Reaction equation

HRID 2406735 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:22]=[CH:21][CH:20]=[CH:19][C:16]=2[C:17]#[N:18])[CH2:11][CH2:10]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[Br:1][C:20]1[CH:21]=[N:22][C:15]([N:12]2[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)=[C:16]([CH:19]=1)[C:17]#[N:18]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 27638522-(Morpholin-4-yl)pyridine-3-carbonitrile

Product 1

HCID 68609793HCID 68609793, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-bromosuccinimide (141 mg) was added to a DMF (3 ml) solution containing 2-morpholinonicotinonitrile (100 mg), followed by stirring at 80° C. for 5 hours. The reaction solution was adjusted to room temperature. Then, aqueous saturated sodium thiosulfate solution was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and then the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=10:1 to 7:3), and a light yellow solid of 5-bromo-2-morpholinonicotinonitrile (120 mg) was thus obtained.

Workup

  1. customwas adjusted to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=10:1 to 7:3)

Sources & evidence

ORD record
ord-aa3461205c604348ac960114bb8908fb
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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