Ammonia → 4-(Trifluoromethyl)cinnamamide

HRID 352071

反応式

HRID 352071 の反応式
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](O)=[O:12])=[CH:5][CH:4]=1.C[N:17](C)C=O.O=S(Cl)Cl.N>C1(C)C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([NH2:17])=[O:12])=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 6880704-(Trifluoromethyl)cinnamic acid

生成物 1

HCID 57090144-(Trifluoromethyl)cinnamamide収率 96%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
47.5 °C

実験手順

(E)-3-(4-(Trifluoromethyl)phenyl)-2-propenoic acid (2400 g, 11.1 mol) and DMF (N,N-dimethylformamide)(82 ml) were added to toluene (12 L). SOCl2 (52.6 mL, 721 mmol) was added dropwise at room temperature and the mixture was stirred at 45-50° C. for 1 hour. The toluene solution cooled to room temperature was added dropwise to 25% aqueous ammonia (12L) at 5-25° C. The mixture was stirred at 45-55° C. for 1 hour. After allowing to cool to room temperature and stirring, the mixture was stirred at the same temperature for 1 hour. The precipitated crystals were collected by filtration, washed with water (12 L) and dried under reduced pressure to give (E)-3-(4-(trifluoromethyl)phenyl)-2-propenamide (2293 g, 10.7 mol, yield 96%).

後処理

  1. stirringThe mixture was stirred at 45-55° C. for 1 hour
  2. temperatureto cool to room temperature
  3. stirringstirring
  4. stirringthe mixture was stirred at the same temperature for 1 hour
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water (12 L)
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-fade97a760ba42528ce90cb5fae54b3d
出典データセット
uspto-grants-2004_06
特許番号
US06743924B2

関連ノート

読み込み中…