Tetrahydrofuran → N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

HRID 1820137

反応式

HRID 1820137 の反応式
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.[CH:11]1([CH2:16][C:17](Cl)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH:6][C:17](=[O:18])[CH2:16][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([CH3:10])[CH:3]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 11430Potassium Carbonate2 回HCID 905494-Bromo-2,6-xylidineHCID 3485182Cyclopentylacetyl chloride

生成物 1

HCID 11507840N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide収率 100%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4-Bromo-2,6-dimethyl-aniline (4.3 g) and cyclopentylacetyl chloride (3.46 g) were mixed in acetonitrile (50 mL) and tetrahydrofuran (20 mL) and the reaction mixture was heated to reflux for 1 hour. Potassium carbonate (4.5 g) was added and the reaction mixture was refluxed for 1 hour and then poured onto crushed ice and saturated aqueous potassium carbonate (50 mL). The product was collected by filtration and washed with water (100 mL) to furnish 6.6 g (100% yield) of the title compound as a solid. LC-MS (m/z) 311 (MH+); tR=3.07, (UV, ELSD) 100%, 100%. 1H NMR (500 MHz, DMSO-d6): 1.21 (m, 2H), 1.52 (m, 2H), 1.61 (m, 2H), 1.77 (m, 2H), 2.11 (s, 6H), 2.25 (m, 1H), 2.31 (d, 2H), 7.27 (s, 2H), 9.23 (s, 1H).

後処理

  1. temperatureto reflux for 1 hour
  2. temperaturethe reaction mixture was refluxed for 1 hour
  3. additionpoured
  4. filtrationThe product was collected by filtration
  5. washwashed with water (100 mL)

出典と根拠

ORDレコード
ord-3620690c7bd44c29b5255e64058b14b4
出典データセット
uspto-grants-2009_10
特許番号
US07601870B2

関連ノート

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