5-(3-Nitrophenyl)furfural → 2-{5-[1-[5-(3-Nitro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid

HRID 2197684

반응식

HRID 2197684 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].[N+:18]([C:21]1[CH:22]=[C:23]([C:27]2[O:31][C:30]([CH:32]=O)=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19].C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[N+:18]([C:21]1[CH:22]=[C:23]([C:27]2[O:31][C:30]([CH:32]=[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:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19]

참가 물질

6

반응물 4

HCID 6124175-(3-Nitrophenyl)furfuralHCID 4594337HCID 4594337, 화합물HCID 10154317Ethylenediamine diacetateHCID 23665763Sodium Bisulfite

생성물 1

HCID 866443012-{5-[1-[5-(3-Nitro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid수율 74.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.092 g, 0.34 mmol), 5-(3-nitrophenyl)furan-2-carbaldehyde (0.071 g, 0.33 mmol) (purchased from Aldrich Chemical Company) and ethylenediamine diacetate (0.059 g, 0.033 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), acetonitrile (1 mL), ether (2×2 mL) and acetonitrile (1 mL). The material was dried in a vacuum oven at 65° C. for 17 h to afford 2-{5-[1-[5-(3-Nitro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (115 mg, 72%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 6.62 (1H, m), 6.90 (1H, m), 7.37 (1H, m), 7.44 (1H, d, J=3.6 Hz), 7.64 (1H, d, J=3.6 Hz), 7.80 (1H, s), 7.88 (1H, m), 7.92 (1H, m), 8.28 (2H, m), 8.65 (1H, m), 10.2 (1H, bs). LC/MS: APCI 466.7, HPLC 96.5%

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), acetonitrile (1 mL), ether (2×2 mL) and acetonitrile (1 mL)
  5. customThe material was dried in a vacuum oven at 65° C. for 17 h

출처 및 근거

ORD 기록
ord-a03c62b184944d779ad22ecd95ee0a6e
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338465B2

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