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

反応式

HRID 2197680 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-10ae44409558468b9c13a01ac7f714eb
出典データセット
uspto-grants-2012_12
特許番号
US08338465B2

関連ノート

読み込み中…