Water → 4,4'-Dichloro-2'-methylbenzanilide

HRID 1016646

反応式

HRID 1016646 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([CH3:19])[CH:13]=1.C(N(CC)CC)C.O>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([Cl:11])=[CH:13][C:14]=2[CH3:19])=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 72514-Chloro-2-toluidineHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chloride

生成物 1

HCID 2952414,4'-Dichloro-2'-methylbenzanilide収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Chlorobenzoyl chloride (19.5 g, 111 mmol) was added over 10 min. to a stirred, cooled (0° C.) solution of 4-chloro-2-methylaniline (15 g, 106 mmol) and triethylamine (22.2 mL, 16.1 g, 159 mmol) in dichloromethane (300 mL) and the mixture was stirred at room temperature for 2 h. Water (100 mL) was added and the dichloromethane was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate (saturated, 200 mL), water (200 mL) and ethyl acetate (1000 mL) were added and the layers were separated. The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with ether and the solid was collected and dried in vacuo to give the title compound (27.3 g, 92%). 1H NMR (360 MHz, CDCl3) δ 7.82 (3H, m), 7.79 (1H, br s), 7.48 (2H, d, J 8.5 Hz), 7.23 (2H, m), and 2.30 (3H, s).

後処理

  1. customthe dichloromethane was evaporated under reduced pressure
  2. additionAqueous sodium hydrogen carbonate (saturated, 200 mL), water (200 mL) and ethyl acetate (1000 mL) were added
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated with ether
  7. customthe solid was collected
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-175a1f612a8a4c78aac9bb2b4b160f6e
出典データセット
uspto-grants-2002_11
特許番号
US06476045B2

関連ノート

読み込み中…