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

HRID 2197681

반응식

HRID 2197681 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].[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

참가 물질

6

반응물 4

HCID 6098215-(2-Chlorophenyl)furfuralHCID 45943372-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acidHCID 10154317Ethylenediamine diacetateHCID 23665763Sodium Bisulfite

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%

후처리

  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

출처 및 근거

ORD 기록
ord-8f1d28d31b87457bb8846e1a576c1406
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338465B2

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