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

HRID 2298879

반응식

HRID 2298879 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fde6fc8e3ab44b2f98e46e198b471392
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495555B1

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