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

HRID 1583702노트

반응식

HRID 1583702 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 17324-Chloro-3-methylphenolHCID 11430Potassium CarbonateHCID 20258046HCID 20258046, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aecff17e9ebd402cb8a972f6dbcf04dd
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04554012

반응 노트

불러오는 중…