Pyridine → HCID 14989652, compound

HRID 1199678Notes

Reaction equation

HRID 1199678 reaction equation
[NH2:1][C:2]1[C:3]([CH2:8][CH2:9][CH2:10][C:11]#[N:12])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>C(#N)C>[C:13]1([S:19]([NH:1][C:2]2[C:3]([CH2:8][CH2:9][CH2:10][C:11]#[N:12])=[N:4][CH:5]=[CH:6][CH:7]=2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 133508363-Aminopyridine-2-butyronitrile

Product 1

HCID 14989652HCID 14989652, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-amino-2-(3-cyanopropyl)pyridine* (5 g, 0.031 mole) in acetonitrile (50 ml) was treated with benzenesulphonyl chloride (4 ml) and pyridine (6 ml). The solution was allowed to stand at room temperature overnight when the solvent was removed in vacuo. The residue was dissolved in dilute sodium hydroxide (100 ml) and was extracted with chloroform (4×100 ml) the chloroform extracts being discarded. The aqueous layer was adjusted to pH=4 and extracted with chloroform (3×100 ml). The combined chloroform extracts were dried over magnesium sulphate, the solvent was removed to give the title compound (7.12 g) as a cream coloured solid. m.p. 80°-81° C.

Workup

  1. customwhen the solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dilute sodium hydroxide (100 ml)
  3. extractionwas extracted with chloroform (4×100 ml) the chloroform
  4. extractionextracted with chloroform (3×100 ml)
  5. dry with materialThe combined chloroform extracts were dried over magnesium sulphate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-d9a94a93daf7462bb22aed836dcdbfc8
Source dataset
uspto-grants-1990_02
Patent number
US04902698

Reaction notes

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