Ammonia → 3-Cyano-5-(trifluoromethyl)benzamide

HRID 623831ノート

反応式

HRID 623831 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7])#[N:2].[NH3:16].C(OCC)(=O)C.CCCCCC>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([NH2:16])=[O:7])#[N:2]

参加物

5

反応物 3

HCID 222AmmoniaHCID 21226206Ethyl acetate hexaneHCID 866720693-Cyano-5-(trifluoromethyl)benzoyl chloride

生成物 1

HCID 675355253-Cyano-5-(trifluoromethyl)benzamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

In 1-neck 250 mL round-bottomed flask, 3-cyano-5-(trifluoromethyl)benzoyl chloride (3.0 g, 1.0 eq.) was dissolved in THF (30 mL, 10 V) at 0° C. Ammonia gas was added and the reaction mixture was stirred for 1-2 h at 0° C. The progress of the reaction was followed by TLC analysis on silica gel with ethyl acetate:hexane (5:5) as mobile phase and visualization with UV, SM Rf=0.10 and Product Rf=0.25. Reaction mixture was quenched into the ice-water slurry (100 mL) and extracted in the ethyl acetate (100 mL×3). Organic layer was washed with brine solution (100 mL) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 2.5 g of crude compound as white solid, yield (88%). This crude 3-cyano-5-(trifluoromethyl)benzamide was directly used for next step without purification; Mass: (ES−) 212.95 (M−1).

後処理

  1. customReaction mixture
  2. customwas quenched into the ice-water slurry (100 mL)
  3. extractionextracted in the ethyl acetate (100 mL×3)
  4. washOrganic layer was washed with brine solution (100 mL)
  5. customby drying
  6. concentrationOrganic layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-56e735ad4d3f419b8eea4b5fa546870f
出典データセット
uspto-grants-2016_04
特許番号
US09303000B2

反応ノート

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