4-Chlorobutyronitrile → 4-[({4-[(Dimethylamino)methyl]pyridin-2-yl}methyl)sulfanyl]butanenitrile
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][CH2:22][C:23]#[N:24].[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][CH2:22][C:23]#[N:24])[CH:9]=1)[CH3:4]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of S-(4-dimethylaminomethyl-2-pyridylmethyl)isothiourea trihydrochloride (11.88 g) and 4-chlorobutyronitrile (5.21 g) in water (50 ml) and ethanol (35 ml) at 0° C. (ice-salt bath) under nitrogen, was added dropwise over 20 minutes a solution of sodium hydroxide (6.4 g) in water (65 ml), keeping the temperature below 5° C. After having been stirred for 5 hours and allowed to stand for 20 hours, the solution was extracted with 3:1 chloroform:ethanol (3×100 ml) and the combined extracts washed with water and dried (MgSO4). Solvent was evaporated at reduced pressure and the residue vacuum-distilled to give 4-(4-dimethylaminomethyl-2-pyridylmethylthio)butyronitrile (7.16 g) as a pale yellow liquid, b.p.0.01 mm 170° C.
Workup
- customthe temperature below 5° C
- waitto stand for 20 hours
- extractionthe solution was extracted with 3:1 chloroform
- washethanol (3×100 ml) and the combined extracts washed with water
- dry with materialdried (MgSO4)
- customSolvent was evaporated at reduced pressure
- distillationthe residue vacuum-distilled
Sources & evidence
- ORD record
- ord-4a2408a71d8e462d9edce91bb4c00eb5
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04808589
Reaction notes
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