2-Bromoaniline → HCID 18350678, 화합물

HRID 430512

반응식

HRID 430512 반응식
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[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:4]([C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[Br:1])[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 119922-BromoanilineHCID 24387Phosphorus trichlorideHCID 28075793-Acetamidothiophene-2-carboxylic acid

생성물 1

HCID 18350678HCID 18350678, 화합물수율 47%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
105 °C

실험 절차

To a mixture of pyridine (6 mL), 2-bromoaniline (1.03 g, 6 mmol), and 3-acetamidothiophene-2-carboxylic acid (0.555 g, 3 mmol) was added phosphorus trichloride (0.03 mL, 3.45 mmol). The reaction was heated to 105° C. for 4 hours, cooled to ambient temperature and partitioned between chloroform and water (an insoluble precipitate was removed by filtration). Phases were separated and the aqueous layer was extracted with chloroform. The combined organic phase was washed with water and brine, dried over magnesium sulfate and concentrated to a dull yellow film. This residue was flash chromatographed on silica gel (30×125 mm) eluting with 15-25% ethyl acetate/hexane to afford 0.411 g (47%) of 2-methyl-3-(2-bromophenyl)-3H-thieno[3,2-d]pyrimidin-4-one as a yellow foam,

후처리

  1. temperaturecooled to ambient temperature
  2. custompartitioned between chloroform and water (an insoluble precipitate
  3. customwas removed by filtration)
  4. customPhases were separated
  5. extractionthe aqueous layer was extracted with chloroform
  6. washThe combined organic phase was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated to a dull yellow film
  9. customchromatographed on silica gel (30×125 mm)
  10. washeluting with 15-25% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-b2bbe11e0c4f44b1a03d598b2dc6143b
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323208B1

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