5-(2-氯苯基)糠醛 → 2-{5-[1-[5-(2-Chloro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid

HRID 2197681

反应方程式

HRID 2197681 反应方程式
[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].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[O:29][C:28]([CH:30]=O)=[CH:27][CH:26]=1.C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[O:29][C:28]([CH:30]=[C:6]2[S:5][C:4](=[S:7])[N:3]([NH:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11]([OH:13])=[O:12])[C:2]2=[O:1])=[CH:27][CH:26]=1

参与物

6

反应物 4

HCID 6098215-(2-氯苯基)糠醛HCID 45943372-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acidHCID 10154317乙二胺二乙酸酯HCID 23665763亚硫酸氢钠

产物 1

HCID 866443002-{5-[1-[5-(2-Chloro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid收率 92%

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

实验过程

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.090 g, 0.34 mmol), 5-(2-chloro-phenyl)-furan-2-carbaldehyde (0.074 g, 0.36 mmol) (purchased from Aldrich Chemical Co.) and ethylenediamine diacetate (0.065 g, 0.036 mmol) in methanol (8 mL) was stirred at room temperature for 17 h. The reaction mixture was poured into stirred 0.6 N aq sodium hydrogensulfite (50 mL). The mixture was vigorously stirred for 15 min. The solid product was filtered off and washed on funnel successively with 0.6 N aq sodium hydrogensulfite (2 mL), water (2×2 mL), ether (2 mL) and hexanes (2 mL). The material was dried in a vacuum oven at 65° C. for 19 h to afford 2-{5-[1-[5-(2-Chloro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (141 mg, 92%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 6.55 (1H, d, J=8.0 Hz), 6.87 (1H, t, J=7.6 Hz), 7.32 (1H, t, J=7.6 Hz), 7.44-7.51 (3H, m), 7.62 (1H, d, J=8.0 Hz), 7.66 (1H, d, J=8.4 Hz), 7.80 (1H, s), 7.91 (1H, d, J=8.0 Hz), 7.97 (1H, d, J=8.0 Hz). LC/MS: APCI 457.2, HPLC 97.9%

后处理

  1. additionThe reaction mixture was poured
  2. stirringThe mixture was vigorously stirred for 15 min
  3. filtrationThe solid product was filtered off
  4. washwashed on funnel successively with 0.6 N aq sodium hydrogensulfite (2 mL), water (2×2 mL), ether (2 mL) and hexanes (2 mL)
  5. customThe material was dried in a vacuum oven at 65° C. for 19 h

来源与证据

ORD记录
ord-8f1d28d31b87457bb8846e1a576c1406
来源数据集
uspto-grants-2012_12
专利号
US08338465B2

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