Dicyclohexylcarbodiimide → HCID 178418733、化合物

HRID 30898

反応式

HRID 30898 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)=[C:16]([F:23])[CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[NH:12][C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=3[N:1]=2)=[C:16]([F:23])[CH:15]=1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 27570034-Bromo-2-fluorophenylisothiocyanate

生成物 1

HCID 178418733HCID 178418733、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

1,2-Diamino-5-trifluoromethylbenzene (0.50 g, 2.84 mmol) was diluted in dichloromethane (5 mL) and treated with 4-bromo-2-fluoro-phenylisothiocyanate (0.66 g, 2.84 mmol). The dark solution was stirred at 45° C. for 15 minutes, then 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol) was added all at once. The reaction was heated in a 45° C. oil bath overnight, then cooled and concentrated at reduced pressure. The dark residue was diluted with ethyl acetate, and the organic layer was washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting dark brown oil was purified by flash chromatography on silica gel eluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate. The title compound was collected as a light pink solid (0.60 g, 57%). 1H NMR (300 MHz, DMSO-d6) δ 11.3 (broad d, 1H), 9.87 (d, 1H), 7.50 (d, 2H), 7.61 (d, 1H), 7.55-7.41 (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 heated in a 45° C. oil bath overnight
  2. temperaturecooled
  3. concentrationconcentrated at reduced pressure
  4. additionThe dark residue was diluted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting dark brown oil was purified by flash chromatography on silica gel
  9. washeluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate
  10. customThe title compound was collected as a light pink solid (0.60 g, 57%)

出典と根拠

ORDレコード
ord-96df1c5f8f534faaa5ac531f3060bf4f
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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