Phosphorus trichloride → HCID 18350679, 화합물

HRID 430511

반응식

HRID 430511 반응식
[NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9]([NH:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18](O)=[O:19])(=O)[CH3:10].P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:10][C:9]1[N:1]([C:2]2[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=2)[C:18](=[O:19])[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[N:12]=1

참가 물질

5

반응물 3

HCID 24387Phosphorus trichlorideHCID 805282-Chloro-3-pyridylamineHCID 28075793-Acetamidothiophene-2-carboxylic acid

생성물 1

HCID 18350679HCID 18350679, 화합물수율 63%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
105 °C

실험 절차

To a mixture of pyridine (4 mL), 3-amino-2-chloropyridine (0.514 g, 4 mmol), and 3-acetamidothiophene-2-carboxylic acid (0.370 g, 4 mmol) was added phosphorus trichloride (0.02 mL, 2.3 mmol). The reaction was heated to 105° C. for 3 hours, cooled to ambient temperature and partitioned between ethyl acetate and water. Phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over sodium sulfate and concentrated to a greenish brown oil. This residue was flash chromatographed on silica gel (20×120 mm) eluting with 20-40% ethyl acetate/hexane to afford 0.350 g (63%) of 2-methyl-3-(2-chloropyrid-3-yl)-3H-thieno[3,2-d]pyrimidin-4-one as a yellow foam.

후처리

  1. temperaturecooled to ambient temperature
  2. custompartitioned between ethyl acetate and water
  3. customPhases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to a greenish brown oil
  8. customchromatographed on silica gel (20×120 mm)
  9. washeluting with 20-40% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-2d0269e9bbed4ddebd146f92e46f6348
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323208B1

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