Sodium Hydroxide → HCID 19099326, compound

HRID 1975472Notes

Reaction equation

HRID 1975472 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[N:5].[CH3:6][S:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11].[OH-].[Na+]>O.O1CCCC1>[CH3:6][S:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:5][CH2:4][C:3]#[N:2])=[O:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 27745172-(Methylsulfanyl)pyridine-3-carbonyl chlorideHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 19099326HCID 19099326, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of aminoacetonitrile hydrochloride (5.95 g) in a mixture of water (100 ml) and tetrahydrofuran (100 ml) was added slowly 2 -(methylthio)nicotinoyl chloride (10 g) at 0° C. while adjusting pH to 8-9 with 4N-aqueous sodium hydroxide. After stirring for 30 minutes at 0° C., the solvent was evaporated to give a residue, which was chromatographed on silica gel (350 ml) eluting with ethyl acetate to give [2-(methylthio)nicotinoyl]aminoacetonitrile (9.9 g).

Workup

  1. customthe solvent was evaporated
  2. customto give a residue, which
  3. customwas chromatographed on silica gel (350 ml)
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-849bb1abe30a4ec0ae06dce5991b1c1f
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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