Ethylenediamine diacetate → HCID 86644295、化合物

HRID 2197673

反応式

HRID 2197673 の反応式
[O:1]=[C:2]1[CH2:6][S:5][C:4](=[S:7])[N:3]1[CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1.[CH2:17]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][C:30]([CH:32]=O)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH:18]([CH3:20])[CH3:19].C(O)(=O)C.C(O)(=O)C.C(N)CN>C(O)C.C(OCC)(=O)C>[CH2:17]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][C:30]([CH:32]=[C:6]3[S:5][C:4](=[S:7])[N:3]([CH:8]4[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]4)[C:2]3=[O:1])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH:18]([CH3:20])[CH3:19]

参加物

6

反応物 3

HCID 10154317Ethylenediamine diacetateHCID 594462253-(4-Oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acidHCID 59446226HCID 59446226、化合物

生成物 1

HCID 86644295HCID 86644295、化合物収率 72%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-(4-oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acid (0.075 g, 0.29 mmol), 5-(4-isobutyl-phenyl)-furan-2-carbaldehyde (0.069 g, 0.30 mmol) and ethylenediamine diacetate (0.057 g, 0.32 mmol) in anhydrous ethanol (12 mL) was stirred 30 h at ambient temperature. The reaction mixture was diluted with ethyl acetate (250 mL) and extracted with 0.6 N aq. sodium hydrogensulfite (2×50 mL). The organic layer was separated, dried over sodium sulfate and concentrated. The residue was triturated with hot acetonitrile (5 mL) and allowed to cool to room temperature. The product was filtered off, washed on the funnel with acetonitrile (0.5 mL) and dried in a vacuum oven at 60° C. for 17 h to afford 3-{5-[1-[5-(4-isobutyl-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-cyclohexanecarboxylic acid (98 mg, 72%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 0.88 (6H, d, J=6.4 Hz), 1.16-1.45 (2H, m), 1.68 (1H, m), 1.84-1.92 (4H, m), 2.25-2.54 (3H, m), 4.98 (1H, m), 7.27 (1H, d, J=3.6 Hz), 7.36 (2H, m), 7.36 (1H, d, J=3.6 Hz), 7.58 (1H, s), 7.77 (2H, m), 12.22 (1H, s). LC/MS: APCI 469.51, HPLC 100%.

後処理

  1. extractionextracted with 0.6 N aq. sodium hydrogensulfite (2×50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with hot acetonitrile (5 mL)
  6. temperatureto cool to room temperature
  7. filtrationThe product was filtered off
  8. washwashed on the funnel with acetonitrile (0.5 mL)
  9. customdried in a vacuum oven at 60° C. for 17 h

出典と根拠

ORDレコード
ord-578468d40da141f28f3d10ed92b038b6
出典データセット
uspto-grants-2012_12
特許番号
US08338465B2

関連ノート

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