Trifluoroacetic acid → HCID 66626031、化合物

HRID 1663268ノート

反応式

HRID 1663268 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([NH2:16])[S:8][C:7]=1[NH2:17])=[O:5])[CH3:2].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH:23]=O.FC(F)(F)C(O)=O>C(O)(C)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([N:16]=[CH:23][C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)[S:8][C:7]=1[NH2:17])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 73642-ThiophenecarboxaldehydeHCID 840025Diethyl 2,5-diaminothiophene-3,4-dicarboxylate

生成物 1

HCID 66626031HCID 66626031、化合物収率 81%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

In a round bottom flask (50 mL), 2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester (50 mg) was added to 20 mL isopropanol to which was added 2-thiophenecarboxaldehyde (24 mg) and a catalytic amount of trifluoroacetic acid (TFA). The mixture was refluxed for 20 hours. Complete removal of the solvent provides an orange solid which was purified by flash chromatography (SiO2), yielding the title compound as an orange solid (81%). M.p.: 114°-116° C. 1H-NMR (300 MHz, [D] acetone): δ=8.24 (s, 1H), 7.63 (d, 1H, 3J=5.0 Hz), 7.52 (dd, 1H, 3J=3.7 Hz and 4J=0.7 Hz), 7.48 (s, 2H), 7.14 (dd, 1H, 3J=5.0 Hz and 3.7 Hz), 4.32 (q, 2H, 3J=7.2 Hz), 4.19 (q, 2H, 3J=7.1 Hz), 1.37 (t, 3H, 3J=7.1 Hz), 1.26 (t, 3H, 3J=7.1 Hz). 13C-NMR (300 MHz, [D] acetone): δ=165.0, 164.3, 161.1, 161.0, 146.1, 143.2, 132.8, 132.1, 130.5, 128.4, 101.8, 61.0, 60.0, 14.3, 14.1.

後処理

  1. temperatureThe mixture was refluxed for 20 hours
  2. customComplete removal of the solvent
  3. customprovides an orange solid which
  4. customwas purified by flash chromatography (SiO2)

出典と根拠

ORDレコード
ord-3e57f0fec68446d89f8904372be54a71
出典データセット
uspto-grants-2011_10
特許番号
US08034895B2

反応ノート

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