3,4,6-Trifluorobenzene-1,2-diamine → HCID 18537794, 화합물

HRID 412728

반응식

HRID 412728 반응식
[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

참가 물질

4

반응물 2

HCID 5956243,4,6-Trifluorobenzene-1,2-diamineHCID 13451607HCID 13451607, 화합물

생성물 1

HCID 18537794HCID 18537794, 화합물수율 42.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cbd479142c1c47c890fa64a146dcdc43
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562854B2

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