5-(3-(Trifluoromethyl)phenyl)furfural → HCID 86644302, 화합물

HRID 2197685

반응식

HRID 2197685 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].[F:18][C:19]([F:34])([F:33])[C:20]1[CH:21]=[C:22]([C:26]2[O:30][C:29]([CH:31]=O)=[CH:28][CH:27]=2)[CH:23]=[CH:24][CH:25]=1.C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[O:1]=[C:2]1[C:6](=[CH:31][C:29]2[O:30][C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:33])([F:18])[F:34])[CH:21]=3)=[CH:27][CH:28]=2)[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]

참가 물질

6

반응물 4

HCID 7218375-(3-(Trifluoromethyl)phenyl)furfuralHCID 4594337HCID 4594337, 화합물HCID 10154317Ethylenediamine diacetateHCID 23665763Sodium Bisulfite

생성물 1

HCID 86644302HCID 86644302, 화합물수율 79%

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-(3-trifluoromethyl-phenyl)-furan-2-carbaldehyde (0.086 g, 0.36 mmol) (purchased from Aldrich Chemical Company) 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 mm. 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-{4-Oxo-2-thioxo-5-[1-[5-(3-trifluoromethyl-phenyl)-furan-2-yl]-methylidene]-thiazolidin-3-ylamino}-benzoic acid (130 mg, 79%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 6.53 (1H, m), 6.86 (1H, m), 7.29 (1H, m), 7.43 (1H, d, J=3.6 Hz), 7.59 (1H, d, J=3.6 Hz), 7.78 (1H, s), 7.82 (2H, m), 7.92 (1H, m), 8.16 (1H, m), 8.21 (1H, m). LC/MS: APCI 489.3, HPLC 97.1%

후처리

  1. additionThe reaction mixture was poured
  2. stirringThe mixture was vigorously stirred for 15 mm
  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-ba19cf6761d3480ab16ffcf3da0d1504
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338465B2

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