3-Fluoro-5-(trifluoromethyl)benzonitrile → 3-(Methylthio)-5-(trifluoromethyl)benzamide

HRID 623823ノート

反応式

HRID 623823 の反応式
F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[C:5]#[N:6].[CH3:14][S-:15].[Na+].C[OH:18].ClCCl>CC(C)=O.O>[CH3:14][S:15][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[C:5]([NH2:6])=[O:18]

参加物

6

反応物 3

HCID 5190373-Fluoro-5-(trifluoromethyl)benzonitrileHCID 4378561Sodium methanethiolateHCID 21226129Dichloromethane methanol

生成物 1

HCID 705577563-(Methylthio)-5-(trifluoromethyl)benzamide

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

In a 500-mL, 3-neck round-bottomed flask equipped with an 100-mL pressure-equalizing addition funnel fitted with an nitrogen inlet, and a rubber septum, 3-fluoro-5-(trifluoromethyl)benzonitrile (8.0 g, 1.0 eq.), in acetone (40 mL). Sodiumthiomethoxide (3.42 g, 1.15 eq) was dissolved in water to make 21% aqueous solution and was added dropwise in 30 min at 5° C. temperature. The temperature of the reaction was slowly raised to RT and stirred for 3 h. Then temperature was raised to 50-60° C. and maintained for further 4-6 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% MeOH-dichloromethane as mobile phase and visualization with UV, SM Rf=0.40 and Product Rf=0.25. Reaction was stirred for 3 hr at 25° C. and 4-6 hrs at 50-60° C. and reaction mixture was transparent. The reaction mass was quench by water and extracted by ethyl acetate (3×100 mL). The combined organic layer was washed with brine 50 mL and dried over sodium sulphate and evaporated on buchi rotaevaporator. The resulting crude compound (8 g) was subjected to further stage Yield (80.9%); Mass: (ES+) 235.94 (M+1).

後処理

  1. customIn a 500-mL, 3-neck round-bottomed flask equipped with an 100-mL pressure-equalizing addition funnel
  2. customfitted with an nitrogen inlet
  3. additionwas added dropwise in 30 min at 5° C. temperature
  4. temperatureThen temperature was raised to 50-60° C.
  5. temperaturemaintained for further 4-6 h
  6. customReaction
  7. stirringwas stirred for 3 hr at 25° C. and 4-6 hrs at 50-60° C.
  8. customreaction mixture
  9. customThe reaction mass was quench by water
  10. extractionextracted by ethyl acetate (3×100 mL)
  11. washThe combined organic layer was washed with brine 50 mL
  12. dry with materialdried over sodium sulphate
  13. customevaporated on buchi rotaevaporator
  14. customYield (80.9%)

出典と根拠

ORDレコード
ord-55b7f741b3ed4f92bd9a83d8c73f4045
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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