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Ammonium formate → HCID 72556533, 화합물

HRID 2217623
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HRID 2217623 반응식
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:33]=[CH:32][C:12]([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20](=[CH:24][C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)[C:21]([OH:23])=[O:22])=[CH:16][CH:15]=3)=[CH:11][CH:10]=2)[S:3]1.C([O-])=O.[NH4+]>C(O)(=O)C.[Pd]>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][C:14]3[CH:15]=[CH:16][C:17]([C:20](=[CH:24][C:25]4[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=4)[C:21]([OH:23])=[O:22])=[CH:18][CH:19]=3)=[CH:32][CH:33]=2)[S:3]1
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참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 725565302-{4-[4-(2,4-Dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-3-p-tolylacrylic acid

생성물 1

HCID 72556533HCID 72556533, 화합물수율 60.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

To a solution of 40 (1.0 g, 2.2 mmol) and ammonium formate (8.32 g, 132 mmol) in 25 mL glacial acetic acid was added 5% Pd/C (1.0 g). The mixture was refluxed for 7.5 h, cooled to room temperature and filtered over Celite. The mixture was concentrated in vacuum then added to 200 mL water. The product was filtered and washed with hexanes. The solid was recrystallized out of toluene, cooled to room temperature and sonicated until the solid was observed. The mixture was then stirred at room temperature for 16 h. The precipitate was collected and washed with hexanes to yield a white solid (0.609 g, 59.1%). 1H NMR (400 MHz, DMSO-d6) δ 12.65 (s, 1H), 12.05 (br s, 1H), 7.72 (s, 1H), 7.30 (d, J=8.8 Hz, 2H), 7.16 (d, J=8.4 Hz, 2H), 7.05 (d, J=8.4 Hz, 2H), 7.01 (d, J=8.4 Hz, 2H), 6.99 (d, J=9.2 Hz, 2H), 6.98 (d, J=8.0 Hz, 2H), 4.92 (dd, J=4.4 and 9.6 Hz, 1H), 3.38 (dd, J=4.4 and 14.0 Hz, 1H), 3.21 (dd, J=9.2 and 14.0 Hz, 1H), 2.24 (s, H).

후처리

  1. temperatureThe mixture was refluxed for 7.5 h
  2. filtrationfiltered over Celite
  3. concentrationThe mixture was concentrated in vacuum
  4. additionthen added to 200 mL water
  5. filtrationThe product was filtered
  6. washwashed with hexanes
  7. customThe solid was recrystallized out of toluene
  8. temperaturecooled to room temperature
  9. customsonicated until the solid
  10. customThe precipitate was collected
  11. washwashed with hexanes

출처 및 근거

ORD 기록
ord-3921b2e66134458e8cf5f6e29f8bcdf0
출처 데이터셋
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07407978B2

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