Propylamine → 5-(5-Chlorobenzoxazol-2-yl)-2-n-propylaminoaniline

HRID 74315

反応式

HRID 74315 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13](F)=[C:14]([N+:16]([O-])=O)[CH:15]=3)=[N:7][C:6]=2[CH:20]=1.C(N(CC)CC)C.[CH2:28]([NH2:31])[CH2:29][CH3:30].[H][H]>C(#N)C.[C].[Pd].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:31][CH2:28][CH2:29][CH3:30])=[C:14]([CH:15]=3)[NH2:16])=[N:7][C:6]=2[CH:20]=1

参加物

8

反応物 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 674975535-Chloro-2-(2-fluoronitrobenzen-5-yl)benzoxazoleHCID 178418361HCID 178418361、化合物

生成物 1

HCID 674986575-(5-Chlorobenzoxazol-2-yl)-2-n-propylaminoaniline収率 97%

試薬・触媒・溶媒 3

HCID 178418390HCID 178418390、化合物触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a suspension of 5-chloro-2-(2-fluoronitrobenzen-5-yl)benzoxazole (see Working Example 100-1) (1.5 g, 5.13 mmol) in acetonitrile (10 mL) was added triethylamine (779 mg, 7.70 mmol) and propylamine (364 mg, 6.16 mmol), and this was heated to reflux for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a solution of the crystals obtained in ethanol/tetrahydrofuran (1:2, 15 mL) was added 10% palladium-carbon (200 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 18 hours. After the reaction was finished, this was filtered through Celite, and the filtrate was concentrated to yield the title compound (1.5 g, 97% yield) as orange crystals.

後処理

  1. temperaturethis was heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a solution of the crystals obtained in ethanol/tetrahydrofuran (1:2, 15 mL)
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-1f02076f3e574d15a642b8b62727a875
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

関連ノート

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