Water → N-(4-Chloro-3-cyanophenyl)acetamide

HRID 1521356ノート

反応式

HRID 1521356 の反応式
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:17])=[C:13]([CH:16]=1)[C:14]#[N:15].C1(C)C=CC=CC=1.O>CCOC(C)=O>[Cl:17][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:5](=[O:7])[CH3:6])=[CH:16][C:13]=1[C:14]#[N:15]

参加物

6

反応物 4

HCID 962WaterHCID 1140TolueneHCID 7918Acetic AnhydrideHCID 109972345-Amino-2-chlorobenzonitrile

生成物 1

HCID 25638344N-(4-Chloro-3-cyanophenyl)acetamide収率 92%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Acetic anhydride (2.79 mL, 29.5 mmol), 5-amino-2-chloro-benzonitrile (3.00 g, 19.7 mmol), N,N-dimethylaminopyridine (0.241 g, 1.97 mmol), and toluene (50 mL) were combined and heated to reflux for 1.5 h. The reaction mixture was cooled, and water and EtOAc (150 mL) were added. The solid remaining in the mixture was collected and set aside. The aqueous layer was extracted once more with EtOAc, and the combined layers were washed with brine. The reserved precipitate was then dissolved in EtOAc, which was washed with brine. All organic layers were combined, dried, filtered, and concentrated. The residue was triturated with DCM/hexanes to yield the titled compound (3.52 g, 92% yield). This compound did not yield MS data. 1H NMR (400 MHz, CDCl3): 7.92 (d, J=1.0 Hz, 1H), 7.57 (dd, J=2.1, 1.2 Hz, 2H), 2.17 (s, 3H).

後処理

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. temperatureThe reaction mixture was cooled
  4. customwas collected
  5. extractionThe aqueous layer was extracted once more with EtOAc
  6. washthe combined layers were washed with brine
  7. dissolutionThe reserved precipitate was then dissolved in EtOAc
  8. washwhich was washed with brine
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was triturated with DCM/hexanes

出典と根拠

ORDレコード
ord-dff92e50219348ba829ffa4f3693b7ac
出典データセット
uspto-grants-2015_07
特許番号
US09073923B2

反応ノート

読み込み中…