Hydrochloric Acid → 2-Methyl-4-(trifluoromethyl)benzonitrile

HRID 1391647

反応式

HRID 1391647 の反応式
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1N.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[C-:24]#[N:25].[K+]>O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].CCOCC>[CH3:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:24]#[N:25]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 137504374-Amino-3-methylbenzotrifluorideHCID 23668193Sodium Nitrite

生成物 1

HCID 222503322-Methyl-4-(trifluoromethyl)benzonitrile収率 88.4%

試薬・触媒・溶媒 3

HCID 24463Copper sulfate pentahydrate触媒HCID 962Water溶媒4 回HCID 3283Diethyl Ether溶媒

反応条件

温度
5 °C

実験手順

Concentrated hydrochloric acid (16 mL) was added dropwise at a moderate rate to a heterogeneous mixture of 2-methyl-4-(trifluoromethyl)benzenamine (14 g, 80 mmol) and 120 mL of water while stirring vigorously. A thick suspension resulted which was stirred for 20 minutes, diluted with 280 mL of water and cooled to 5° C. A solution of sodium nitrite (5.5 g, 80 mmol) and 25 mL of water was added slowly to the reaction suspension. After stirring for 30 minutes at 5° C. a solution resulted which was stirred cold for 30 more minutes and then neutralized with potassium carbonate. This diazonium salt solution was then added portionwise via cannula to a stirred, 95° C. mixture of potassium cyanide (22 g, 0.34 mole), copper sulfate pentahydrate (20 g, 80 mmol) and 140 mL of water. After the addition the mixture was stirred for 30 minutes at 95° C. and then allowed to cool to room temperature. Ether was added and the heterogeneous mixture was filtered through celite. The solids were washed with ether, and the filtrate was partitioned. The aqueous phase was extracted with ether, and the combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to afford 13.1 g of the title compound as brown oil.

後処理

  1. customA thick suspension resulted which
  2. stirringwas stirred for 20 minutes
  3. stirringAfter stirring for 30 minutes at 5° C. a solution
  4. customresulted which
  5. stirringwas stirred cold for 30 more minutes
  6. additionAfter the addition the mixture
  7. stirringwas stirred for 30 minutes at 95° C.
  8. temperatureto cool to room temperature
  9. filtrationthe heterogeneous mixture was filtered through celite
  10. washThe solids were washed with ether
  11. customthe filtrate was partitioned
  12. extractionThe aqueous phase was extracted with ether
  13. dry with materialthe combined organic extracts were dried over magnesium sulfate
  14. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-222c44f108ff4f4fb02dc808803e7118
出典データセット
uspto-grants-2008_03
特許番号
US07338978B2

関連ノート

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