Ethyl Acetate → 2-Methyl-propane-2-sulfinic acid[1-(6-chloro-pyridazin-3-yl)-1-methyl-ethyl]-amide

HRID 2038762ノート

反応式

HRID 2038762 の反応式
[Cl:1][C:2]1[N:7]=[N:6][C:5](/[C:8](=[N:10]/[S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])/[CH3:9])=[CH:4][CH:3]=1.[CH3:17][Mg]Br.[NH4+].[Cl-].CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH:10][S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])([CH3:17])[CH3:9])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 88959216(NE)-N-[1-(6-chloropyridazin-3-yl)ethylidene]-2-methylpropane-2-sulfinamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 889591792-Methyl-propane-2-sulfinic acid[1-(6-chloro-pyridazin-3-yl)-1-methyl-ethyl]-amide収率 24.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

Crude 2-methyl-propane-2-sulfinic acid[1-(6-chloro-pyridazin-3-yl)-eth-(E)-ylidene]-amide (56 mg, 0.22 mmol) was dissolved in dry THF (2.2 mL) and cooled to −20° C. under an atmosphere of inert gas. Methylmagnesium bromide (1.0 M in MePh/THF, 0.26 mL, 0.26 mmol) was added in one portion via syringe and the reaction was stirred −20° C. for 1.5 h. To the reaction mixture was added saturated aqueous NH4Cl (4 mL) and EtOAc (7 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organic layers were dried over Na2SO4, concentrated and then purified by flash chromatography (silica, 0→4% MeOH/CH2Cl2). 15 mg of impure 2-methyl-propane-2-sulfinic acid[1-(6-chloro-pyridazin-3-yl)-1-methyl-ethyl]-amide was isolated as a light brown solid. This material was used without further purification.

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×5 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (silica, 0→4% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-1beb133377424500a9b65bec9d742398
出典データセット
uspto-grants-2013_11
特許番号
US08575360B2

反応ノート

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