Hydrochloric Acid → 2-Chloro-6-(2,4-difluorophenylthio)nicotinonitrile

HRID 334418

反応式

HRID 334418 の反応式
[OH-].[K+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[SH:11].[Cl:12][C:13]1[N:20]=[C:19](Cl)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].Cl>C(O)C.O>[Cl:12][C:13]1[N:20]=[C:19]([S:11][C:5]2[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:4]=2[F:3])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27370732,4-Difluorobenzene-1-thiolHCID 126055382,6-Dichloropyridine-3-carbonitrile

生成物 1

HCID 866805632-Chloro-6-(2,4-difluorophenylthio)nicotinonitrile収率 66%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒3 回HCID 962Water溶媒

実験手順

A solution of 362 mg (1.05 eq) of potassium hydroxide in 10 mL of ethanol is added, under nitrogen, to a solution of 698 μL (6.16 mmol) of 2,4-difluorobenzenethiol in 30 mL of ethanol. The reaction medium is stirred at room temperature for 15 minutes and then cooled in ice before adding a solution of 1.015 g (0.95 eq) of 2,6-dichloronicotinonitrile in 30 mL of ethanol. The reaction medium is stirred for 2 hours at 0-5° C. 63 mL of a 0.1N HCl solution is added to stop the reaction. Water is added and the producted is extracted with ethyl acetate. The organic phase is dried on anhydrous magnesium sulfate, filtered and evaporated. The residue is purified by silica gel chromatography (eluent: cyclohexane/ethyl acetate 94:6) to yield 1.09 g (66%) of 2-chloro-6-(2,4-difluorophenylthio)-nicotinonitrile in the form of a white solid.

後処理

  1. temperaturecooled in ice
  2. stirringThe reaction medium is stirred for 2 hours at 0-5° C
  3. customthe reaction
  4. extractionthe producted is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried on anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by silica gel chromatography (eluent: cyclohexane/ethyl acetate 94:6)

出典と根拠

ORDレコード
ord-3bc7bc0b9b2d446d9bd68515daf4eecd
出典データセット
uspto-grants-2014_11
特許番号
US08883821B2

関連ノート

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