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p-Anisoyl chloride → HCID 11248427, 화합물

HRID 1986357
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HRID 1986357 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([O:8][C:9]2[N:14]=[CH:13][C:12]3[N:15]=[C:16]([C:20]4[C:21]([NH2:25])=[N:22][O:23][N:24]=4)[N:17]([CH2:18][CH3:19])[C:11]=3[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1>CN(C=O)C.O.CCOC(C)=O>[NH2:25][C:21]1[C:20]([C:16]2[N:17]([CH2:18][CH3:19])[C:11]3[CH:10]=[C:9]([O:8][C:4]4[CH:3]=[C:2]([NH:1][C:39](=[O:40])[C:38]5[CH:42]=[CH:43][C:35]([O:34][CH3:33])=[CH:36][CH:37]=5)[CH:7]=[CH:6][CH:5]=4)[N:14]=[CH:13][C:12]=3[N:15]=2)=[N:24][O:23][N:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 11404963HCID 11404963, 화합물

생성물 1

HCID 11248427HCID 11248427, 화합물수율 21%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

실험 절차

To a 0° C. solution of 0.10 g of the product of Example 3 (0.30 mmols) in DMF (1.0 mL) was added 0.041 mL of triethylamine (0.30 mmols) and 0.056 g of 4-methoxybenzoylchloride (0.33 mmols). The reaction mixture was allowed to warm to rt and stirred for 23 h. The reaction mixture was diluted with 1 mL of water and 5 mL of EtOAc. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organics were washed with water and concentrated to a partial volume. Methanol was added, and a solid precipitated from the solution. The precipitate was filtered off and dried and the crude product was purified by silica gel chromatography to provide the title compound as a white powder (0.029 g, 21%). MS (ES+) m/e 473 [M+H]+.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organics were washed with water
  4. concentrationconcentrated to a partial volume
  5. additionMethanol was added
  6. customa solid precipitated from the solution
  7. filtrationThe precipitate was filtered off
  8. customdried
  9. customthe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-0f7457204ff94902ac87865048294006
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07547779B2

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