3,4,6-Trifluorobenzene-1,2-diamine → HCID 18537794、化合物

HRID 412728

反応式

HRID 412728 の反応式
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[NH2:11].C(O[C:15]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=N)C>C(O)C>[F:8][C:7]1[C:2]2[N:1]=[C:15]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:11][C:3]=2[C:4]([F:10])=[C:5]([F:9])[CH:6]=1

参加物

4

反応物 2

HCID 5956243,4,6-Trifluorobenzene-1,2-diamineHCID 13451607HCID 13451607、化合物

生成物 1

HCID 18537794HCID 18537794、化合物収率 42.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1,2-diamino-3,4,6-trifluorobenzene (1.92 g, 11.8 mmol), ethyl 2-ethoxycarbonimidoylpropionate (3.1 g, 14.7 mmol) and absolute ethanol (6 ml) was heated at reflux until no further progression of the reaction was indicated by TLC indicated the reaction was not progressing further, filtered from NH4Cl and concentrated. The residue was purified by chromatography on silica (hexane: methylene chloride: ethyl acetate, 5:5:1) to give ethyl 2-(4,6,7-trifluoro-1H-benzoimidazol-2-yl)propionate (1.37 g, 42%) as a tan crystalline solid; NMR (CDCl3): δ 10.35 (s, ½H), δ 7.05 (s, ½H), 6.7 (m, 1H), δ 4.25 (dd, 2H), δ 4.15 (dd, 1H), δ 1.73 (d, 3H), δ 1.31 (t, 3H); M+ 272.9 (calcd for C12H11F3N2O2: 272.23).

後処理

  1. temperaturewas heated
  2. temperatureat reflux until no further progression of the reaction
  3. filtrationfiltered from NH4Cl
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica (hexane: methylene chloride: ethyl acetate, 5:5:1)

出典と根拠

ORDレコード
ord-cbd479142c1c47c890fa64a146dcdc43
出典データセット
uspto-grants-2003_05
特許番号
US06562854B2

関連ノート

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