Sodium Carbonate → 3,4-dihydrobenzothieno[2,3-c]-pyridine-2(1H)-butanenitrile

HRID 2298879

Reaction equation

HRID 2298879 reaction equation
[CH2:1]1[C:6]2[S:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH2:4][CH2:3][NH:2]1.C([O-])([O-])=O.[Na+].[Na+].Cl[CH2:21][CH2:22][CH2:23][C:24]#[N:25]>C(#N)C.CC1C=CC=CC=1>[CH2:1]1[C:6]2[S:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH2:4][CH2:3][N:2]1[CH2:21][CH2:22][CH2:23][C:24]#[N:25]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 123364-ChlorobutyronitrileHCID 4132821,2,3,4-Tetrahydro[1]benzothieno[2,3-c]pyridine

Product 1

HCID 183789583,4-dihydrobenzothieno[2,3-c]-pyridine-2(1H)-butanenitrileYield 101.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-[1]benzothieno[2,3-c]pyridine (0.02 mol), Na2CO3 (5 g), KI (0.1 g) and 4-chlorobutanenitrile (0.025 mol) in acetonitrile (50 ml) and methylbenzene (150 ml) was stirred and refluxed overnight, then cooled, filtered and the filtrate was evaporated. The residue (oil) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated, yielding 5.2 g of 3,4-dihydrobenzothieno[2,3-c]-pyridine-2(1H)-butanenitrile (interm. 6).

Workup

  1. temperaturerefluxed overnight
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe residue (oil) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fde6fc8e3ab44b2f98e46e198b471392
Source dataset
uspto-grants-2002_12
Patent number
US06495555B1

Linked notes

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