Dabco → O-(2,6-Dichloro-4-nitrophenyl) dimethylcarbamothioate

HRID 271208

反応式

HRID 271208 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[OH:12].N12CCN(CC1)CC2.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[S:24]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[O:12][C:23](=[S:24])[N:22]([CH3:26])[CH3:21]

参加物

6

反応物 3

HCID 9237DabcoHCID 120662,6-Dichloro-4-nitrophenolHCID 27871Dimethylthiocarbamoyl chloride

生成物 1

HCID 12661482O-(2,6-Dichloro-4-nitrophenyl) dimethylcarbamothioate収率 75.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

A solution of 2,6-dichloro-4-nitro-phenol (3.0 g, 14.4 mmol) in N,N-dimethylformamide (70 mL) at 25° C. was treated with 1,4-diazabicyclo[2.2.2]octane (3.16 mL, 28.8 mmol) and dimethylthiocarbamoyl chloride (2.85 g, 23.04 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was diluted with ethyl acetate (250 mL) and was then washed with a 1N aqueous hydrochloric acid solution (1×125 mL), water (1×125 mL), and a saturated aqueous sodium chloride solution (1×125 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80:20 petroleum ether/ethyl acetate) afforded dimethyl-thiocarbamic acid O-(2,6-dichloro-4-nitro-phenyl) ester (79) (3.2 g, 75%) as a white solid; EI-LRMS for C9H8Cl2N2O3S (M−Cl)+ at m/z=259. Exact Mass=293.9633; Molecular weight=295.15

後処理

  1. washwas then washed with a 1N aqueous hydrochloric acid solution (1×125 mL), water (1×125 mL)
  2. dry with materiala saturated aqueous sodium chloride solution (1×125 mL), dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-23fff049344b490f97e064bf88e5f05b
出典データセット
uspto-grants-2008_11
特許番号
US07452882B2

関連ノート

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