3-Chloropropionitrile → 3-[({4-[(Dimethylamino)methyl]pyridin-2-yl}methyl)sulfanyl]propanenitrile

HRID 1382769Notes

Reaction equation

HRID 1382769 reaction equation
Cl.Cl.Cl.[CH3:4][N:5]([CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][C:16](=N)N)[CH:9]=1)[CH3:6].ClC[CH2:21][C:22]#[N:23].[OH-].[Na+]>O.C(O)C>[CH3:6][N:5]([CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][CH2:16][CH2:21][C:22]#[N:23])[CH:9]=1)[CH3:4]

Participants

6

Reactant 3

HCID 109633-ChloropropionitrileHCID 14798Sodium HydroxideHCID 21273288S-(4-dimethylaminomethyl-2-pyridylmethyl)isothiourea trihydrochloride

Product 1

HCID 198704133-[({4-[(Dimethylamino)methyl]pyridin-2-yl}methyl)sulfanyl]propanenitrileYield 89.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of S-(4-dimethylaminomethyl-2pyridylmethyl)isothiourea trihydrochloride (21.54 g) and 3-chloropropionitrile (8.01 g) in water (90 ml) and ethanol (65 ml) at 0° C (ice-salt bath) under nitrogen, was added dropwise over 30 minutes, a solution of sodium hydroxide (11.5 g) in water (120 ml), keeping the temperature below 3° C. After having been stirred for 7 hours and allowed to stand for 20 hours, the solution was extracted with 3:1 chloroform:ethanol (3×160 ml). The combined extracts were washed with water and dried (MgSO4) Solvent was evaporated at reduced pressure and the residue vacuum-distilled to give 3-(4-dimethylaminomethy-2-pyridyl-methylthio)propionitrile (13.66 g) as a pale yellow liquid, b.p.0.005 mm 148°-152° C.

Workup

  1. customthe temperature below 3° C
  2. waitto stand for 20 hours
  3. extractionthe solution was extracted with 3:1 chloroform
  4. washThe combined extracts were washed with water
  5. dry with materialdried (MgSO4) Solvent
  6. customwas evaporated at reduced pressure
  7. distillationthe residue vacuum-distilled

Sources & evidence

ORD record
ord-6f4bc160a22049c397314a0735223e8c
Source dataset
uspto-grants-1989_02
Patent number
US04808589

Reaction notes

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