Phosphorus oxide (P4O10) → 7-Phenyl-4,5-dihydrothieno[2,3-c]pyridine

HRID 507699노트

반응식

HRID 507699 반응식
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:2]1.P(Cl)(Cl)(Cl)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[C:10]1([C:9]2[C:2]3[S:1][CH:5]=[CH:4][C:3]=3[CH2:6][CH2:7][N:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

4

반응물 3

HCID 14812Phosphorus oxide (P4O10)HCID 24813Phosphorus oxychlorideHCID 25854160N-(2-(thiophen-3-yl)ethyl)benzamide

생성물 1

HCID 574288827-Phenyl-4,5-dihydrothieno[2,3-c]pyridine수율 92.6%

실험 절차

N-(2-(Thiophen-3-yl)ethyl)benzamide (1.5 g, 6.48 mmol) suspended in xylenes (20 mL) was treated with phosphorous oxychloride (3.62 mL, 38 mmol) and phosphorous pentoxide (5.39 g, 19 mmol). The mixture was heated to reflux for 3 h and the volatiles were removed in vacuo. The residue was diluted with cold water and ethyl acetate. 5 N sodium hydroxide was added and the mixture and the layers were separated. The aqueous layer was extracted twice more with ethyl acetate. All the organic layers were combined and washed with aqueous solution of sodium bicarbonate, water, then brine. The organic layer was dried with sodium sulfate and purified by flash chromatography using a gradient of 20 to 60% of ethyl acetate in hexanes to afford a light yellow clear oil (1.28 g). MS (M+H)+ 214.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. customthe volatiles were removed in vacuo
  4. additionThe residue was diluted with cold water and ethyl acetate
  5. addition5 N sodium hydroxide was added
  6. customthe mixture and the layers were separated
  7. extractionThe aqueous layer was extracted twice more with ethyl acetate
  8. washwashed with aqueous solution of sodium bicarbonate, water
  9. dry with materialThe organic layer was dried with sodium sulfate
  10. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-4cce2018a5934855a1e8aeeef4b64dff
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

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