Toluene → (Pyridin-2-yl)(thiophen-2-yl)acetonitrile
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]#[N:8].Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C1(C)C=CC=CC=1.[NH2-].[Na+]>O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:7]#[N:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a well-stirred solution containing 61.5 g. of 2-thienylacetonitrile and 56.5 g. of 2-chloropyridine in 400 ml. of toluene, slowly add a stirred suspension of 40 g. of sodamide in 300 ml. of toluene keeping the reaction temperature at 60°-65° C by cooling with an ice bath. After completing the addition maintain the temperature at 60° C for 2 hrs., add 200 ml. of water to the cooled reaction mixture, decant the tarry by-products and separate the aqueous layer. Evaporate in vacuo the resulting solution and dilute the thick black residue with 300 ml. of ether. Filter the separated solid and evaporate the filtrate. The desired product is distilled off at 145°-150° C/1 ml. and is recrystallized from alcohol to yield α-(2-thienyl)-2-pyridylacetonitrile, m.p. 48°-50° C.
Workup
- additionTo a well-stirred solution containing 61.5 g
- additiona stirred suspension of 40 g
- additionthe addition
- addition, add 200 ml
- customdecant the tarry by-products
- customseparate the aqueous layer
- customEvaporate in vacuo the resulting solution
- additiondilute the thick black residue with 300 ml
- filtrationFilter the separated solid
- customevaporate the filtrate
- distillationThe desired product is distilled off at 145°-150° C/1 ml
- customand is recrystallized from alcohol
Sources & evidence
- ORD record
- ord-a47b637acb114e378a2f5e40e5097bfd
- Source dataset
- uspto-grants-1978_03
- Patent number
- US04081544
Reaction notes
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