5-(3-(Trifluoromethyl)phenyl)furfural → HCID 86644302、化合物

HRID 2197685

反応式

HRID 2197685 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].[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]

参加物

6

反応物 4

HCID 7218375-(3-(Trifluoromethyl)phenyl)furfuralHCID 4594337HCID 4594337、化合物HCID 10154317Ethylenediamine diacetateHCID 23665763Sodium Bisulfite

生成物 1

HCID 86644302HCID 86644302、化合物収率 79%

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 (0.090 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%

後処理

  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

出典と根拠

ORDレコード
ord-ba19cf6761d3480ab16ffcf3da0d1504
出典データセット
uspto-grants-2012_12
特許番号
US08338465B2

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