Acetic Acid → N-(N-formyl-N-methyl-aminomethyl)-3,4-dichloroisothiazole-5-carboxamide

HRID 642918ノート

反応式

HRID 642918 の反応式
[CH:1]([N:3]([CH3:6])[CH2:4][OH:5])=O.[Cl:7][C:8]1[C:12]([Cl:13])=[C:11]([C:14]([NH2:16])=[O:15])[S:10][N:9]=1.C(O)(=O)C.S(=O)(=O)(O)O>O>[CH:4]([N:3]([CH2:1][NH:16][C:14]([C:11]1[S:10][N:9]=[C:8]([Cl:7])[C:12]=1[Cl:13])=[O:15])[CH3:6])=[O:5]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 107853N-(Hydroxymethyl)-N-methylformamideHCID 113330673,4-Dichloro-5-isothiazolecarboxylic acid amide

生成物 1

HCID 9860156N-(N-formyl-N-methyl-aminomethyl)-3,4-dichloroisothiazole-5-carboxamide収率 47.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

At room temperature, 15 g (0.164 mol) of N-formyl-N-hydroxymethyl-methylamine are added with stirring to a mixture of 32.3 g (0.164 mol) of 3,4-dichloro-isothiazole-5-carboxamide and 245 ml of glacial acetic acid. At room temperature, 37 g (0.362 mol) of concentrated sulphuric acid are then added dropwise with stirring, the reaction mixture being cooled with ice. The reaction mixture is subsequently stirred at room temperature for 29 hours and then, with ice-cooling, admixed with 400 ml of water. The resulting mixture is extracted four times with 200 ml of methylene chloride and the combined organic phases are dried over sodium sulphate and then concentrated under reduced pressure. The oily residue that remains is chromatographed over silica gel using ethyl acetate. Concentration of the eluate gives 20.7 g (42.6% of theory) of N—(N-formyl-N-methyl-aminomethyl)-3,4-dichloro-isothiazole-5-carboxamide in the form of a crystalline solid of melting point 87 to 88° C.

後処理

  1. temperaturethe reaction mixture being cooled with ice
  2. stirringThe reaction mixture is subsequently stirred at room temperature for 29 hours
  3. extractionThe resulting mixture is extracted four times with 200 ml of methylene chloride
  4. dry with materialthe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe oily residue that remains is chromatographed over silica gel

出典と根拠

ORDレコード
ord-9ebc86a3943146d48a4240e0bf05271c
出典データセット
uspto-grants-2010_04
特許番号
US07696355B2

反応ノート

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