1-(3-Bromopropoxy)-4-fluorobenzene → 3-(4-Bromo-benzyl)-1-[3-(4-fluoro-phenoxy)-propyl]-5-methyl-1,3-dihydrobenzoimidazol-2-ylideneamine, hydrobromide salt

HRID 410356

反応式

HRID 410356 の反応式
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=3[NH:9][C:8]2=[NH:17])=[CH:4][CH:3]=1.Br[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1>CC(=O)CC>[BrH:1].[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=3[N:9]([CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[C:8]2=[NH:17])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 2600041-(3-Bromopropoxy)-4-fluorobenzene2 回HCID 1784234951-(4-Bromo-benzyl)-6-methyl-1,3-dihydro-benzoimidazol-2-ylideneamine

生成物 1

HCID 1317316393-(4-Bromo-benzyl)-1-[3-(4-fluoro-phenoxy)-propyl]-5-methyl-1,3-dihydrobenzoimidazol-2-ylideneamine, hydrobromide salt収率 33.1%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒2 回

実験手順

To a solution of 1-(4-bromo-benzyl)-6-methyl-1,3-dihydro-benzoimidazol-2-ylideneamine (0.14 g, 0.44 mmol) in 2-butanone (5 ml) at rt was added 1-(3-bromo-propoxy)-4-fluoro-benzene (0.15 g, 0.66 mmol). The reaction was stirred for 10 min and then additional 2-butanone (5 ml) was introduced. The mixture was heated to reflux where it was maintained for 48 h. After this time, the reaction was cooled to rt and additional 1-(3-bromo-propoxy)-4-fluoro-benzene (0.05, 0.22 mmol) was added. The reaction was then heated to reflux for a further 15 h. It was then cooled to rt and filtered. The collected solid was dried to provide 3-(4-bromo-benzyl)-1-[3-(4-fluoro-phenoxy)-propyl]-5-methyl-1,3-dihydrobenzoimidazol-2-ylideneamine, hydrobromide salt (0.04 g, 16%). HPLC-MS 468, 470 [M+1]+.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux where it
  3. temperaturewas maintained for 48 h
  4. temperatureThe reaction was then heated
  5. temperatureto reflux for a further 15 h
  6. temperatureIt was then cooled to rt
  7. filtrationfiltered
  8. customThe collected solid was dried

出典と根拠

ORDレコード
ord-742fe5ff1016404b89c8dad0a1fdc0d1
出典データセット
uspto-grants-2014_06
特許番号
US08759520B2

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