2-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid → 2-{5-[1-[5-(5-tert-Butyl-2-hydroxy-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid

HRID 2197680

반응식

HRID 2197680 반응식
[O:1]=[C:2]1[CH2:6][S:5][C:4](=[S:7])[N:3]1[NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].[C:18]([C:22]1[CH:23]=[CH:24][C:25]([OH:35])=[C:26]([C:28]2[O:32][C:31]([CH:33]=O)=[CH:30][CH:29]=2)[CH:27]=1)([CH3:21])([CH3:20])[CH3:19].C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([OH:35])=[C:26]([C:28]2[O:32][C:31]([CH:33]=[C:6]3[S:5][C:4](=[S:7])[N:3]([NH:8][C:9]4[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=4[C:11]([OH:13])=[O:12])[C:2]3=[O:1])=[CH:30][CH:29]=2)[CH:27]=1)([CH3:21])([CH3:20])[CH3:19]

참가 물질

6

반응물 4

HCID 45943372-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acidHCID 10154317Ethylenediamine diacetateHCID 23665763Sodium BisulfiteHCID 594462335-(5-Tert-butyl-2-hydroxy-phenyl)-furan-2-carbaldehyde

생성물 1

HCID 866442992-{5-[1-[5-(5-tert-Butyl-2-hydroxy-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid수율 94%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.078 g, 0.29 mmol), 5-(5-tert-butyl-2-hydroxy-phenyl)-furan-2-carbaldehyde and (0.075 g, 0.31 mmol) and ethylenediamine diacetate (0.056 g, 0.031 mmol) in methanol (10 mL) was stirred at room temperature for 18 h. The reaction mixture was poured into stirred 0.6 N aq sodium hydrogensulfite (50 mL). The mixture was vigorously stirred for 30 min. The solid product was filtered off and washed on funnel successively with 0.6 N aq sodium hydrogensulfite (1 mL), water (2×2 mL), ether (2×1 mL) and hexanes (2 mL). The material was dried in a vacuum oven at 65° C. for 17 h to afford 2-{5-[1-[5-(5-tert-Butyl-2-hydroxy-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (135 mg, 94%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 1.37 (9H, s), 6.98 (1H, d, J=8.4 Hz), 7.23 (1H, d, J=3.6 Hz), 7.34 (1H, dd, J=8.8, 2.8 Hz), 7.39 (1H, d, J=3.6 Hz), 7.70 (2H, m), 7.74 (1H, s), 7.94 (1H, d, J=2.4 Hz), 8.01 (1H, m), 8.07 (1H, m). LC/MS. APCI 493.1, HPLC 100%.

후처리

  1. additionThe reaction mixture was poured
  2. stirringThe mixture was vigorously stirred for 30 min
  3. filtrationThe solid product was filtered off
  4. washwashed on funnel successively with 0.6 N aq sodium hydrogensulfite (1 mL), water (2×2 mL), ether (2×1 mL) and hexanes (2 mL)
  5. customThe material was dried in a vacuum oven at 65° C. for 17 h

출처 및 근거

ORD 기록
ord-10ae44409558468b9c13a01ac7f714eb
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338465B2

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