Water → O-4-chloro-3-methylphenyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate

HRID 1583702

反応式

HRID 1583702 の反応式
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)[C:3](Cl)=[S:4].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[CH3:21].C(=O)([O-])[O-].[K+].[K+].O>C(C(C)=O)C>[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)[C:3](=[S:4])[O:20][C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[C:15]([CH3:21])[CH:16]=1

参加物

6

反応物 4

HCID 962WaterHCID 17324-Chloro-3-methylphenolHCID 11430Potassium CarbonateHCID 20258046HCID 20258046、化合物

生成物 1

HCID 13489304O-4-chloro-3-methylphenyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate収率 35%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

A mixture of 2.01 g of N-methyl-N-(6-methyl-2-pyridyl)thiocarbamoylchloride, 1.43 g of 4-chloro-3-methylphenol, and 1.38 g of potassium carbonate in 50 ml of methyl ethyl ketone was refluxed for 48 hours. After the reaction mixture was cooled to room temperature, it was poured into cold water and the product was extracted with benzene. The benzene solution, successively washed with water and brine, was dried over anhydrous magnesium sulfate. The residue obtained by the removal of benzene under reduced pressure was chromatographed through silica gel column using hexane-ethyl acetate (3/1, V/V) as an eluent to give 1.07 g of pure O-4-chloro-3-methylphenyl N-methyl-N-(6-methyl-2-pyridyl)thiocarbamate as solid in the yield of 35%. A part of the solid was recrystallized from benzene-hexane and crystalls having melting point of 134° to 136° C. were obtained.

後処理

  1. temperaturewas refluxed for 48 hours
  2. extractionthe product was extracted with benzene
  3. washThe benzene solution, successively washed with water and brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customThe residue obtained by the removal of benzene under reduced pressure
  6. customwas chromatographed through silica gel column

出典と根拠

ORDレコード
ord-aecff17e9ebd402cb8a972f6dbcf04dd
出典データセット
uspto-grants-1985_11
特許番号
US04554012

関連ノート

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