Citric Acid → 4-[4-(2,4-Dioxothiazolidin-5-ylmethyl)-phenoxy]-benzaldehyde

HRID 2238268

반응식

HRID 2238268 반응식
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.F[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.C(OCC)(=O)C>[O:12]=[C:10]1[NH:9][C:8](=[O:13])[CH:7]([CH2:6][C:5]2[CH:14]=[CH:15][C:2]([O:1][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=3)=[CH:3][CH:4]=2)[S:11]1

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dione

생성물 1

HCID 597682934-[4-(2,4-Dioxothiazolidin-5-ylmethyl)-phenoxy]-benzaldehyde수율 65.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a solution of 52 (5.35 g, 24 mmol) in DMF (150 mL) was added 4-fluorobenzaldehyde (3.00 g, 24 mmol) and Cs2CO3 (20 g, 62 mmol) and the mixture was heated to 100° C. for 2 h. The mixture was poured over vigorously stirring 10% citric acid (200 mL) and ethyl acetate (200 mL). The organic layer was washed with water (300 mL), brine (300 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was triturated in hexanes-ethyl acetate (2:1) to yield a white solid (5.15 g, 65%). 1H NMR: (400 MHz, DMSO-d6): δ 12.07 (bs, 1H), 9.92 (s, 1H), 7.92 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.4 Hz, 2H), 7.09 (d, J=8.4 Hz, 2H) 4.94 (dd, J=8.4 and 4.4 Hz, 1H), 3.41 (dd, J=14.4 and 4.4 Hz, 1H), 3.17 (dd, J=14.4 and 9.2 Hz, 1H).

후처리

  1. additionThe mixture was poured
  2. washThe organic layer was washed with water (300 mL), brine (300 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was triturated in hexanes-ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-3f8585b470fd48e1bfaebd86db09f900
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718682B2

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