Dicyclohexylcarbodiimide → N-(4-bromophenyl)-6-(trifluoromethyl)-1H-benzimidazol-2-amine

HRID 30897

反応式

HRID 30897 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH2:12].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=S)=[CH:16][CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[NH:1][C:2]3[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=3[N:12]=2)=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 161334-Bromophenyl isothiocyanateHCID 5208224-Trifluoromethyl-1,2-phenylenediamine

生成物 1

HCID 21985819N-(4-bromophenyl)-6-(trifluoromethyl)-1H-benzimidazol-2-amine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

1,2-Diamino-5-trifluoromethylbenzene (0.25 g, 1.42 mmol) was diluted in toluene (5 mL) and treated with 4-bromophenylisothiocyanate (0.30 g, 1.42 mmol). The dark solution was stirred at 100° C. for 15 minutes, then treated with 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol). The reaction was maintained at 100° C. for 5 h. The reaction was concentrated and partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4), and concentrated under reduced pressure. The dark brown oil was purified by flash chromatography on silica gel, eluting with a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate. The title compound was obtained as a light pink solid (0.50 g, 30%). 1H NMR (300 MHz, DMSO-d6) δ 11.3 (broad d, 1H), 9.87 (d, 1H), 7.50 (d, 2H), 7.61 (d, 1H), 7.55-7.42 (m, 3H), 7.35-7.30 (m, 1H); LC/MS m/z 356.2 (MH+), retention time 2.33 minutes.

後処理

  1. temperatureThe reaction was maintained at 100° C. for 5 h
  2. concentrationThe reaction was concentrated
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe dark brown oil was purified by flash chromatography on silica gel
  8. washeluting with a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate

出典と根拠

ORDレコード
ord-872e5348f1b346b094f0d6394ac9cd56
出典データセット
uspto-grants-2008_09
特許番号
US07423156B2

関連ノート

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