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Cesium carbonate → 2-Phenylthiomethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 2396790
ノート
印刷プレビュー

反応式

HRID 2396790 の反応式
[Cs].[CH3:2][CH:3]([CH3:15])[CH2:4][CH2:5][CH:6]1[N:10]([CH3:11])[S:9](=[O:13])(=[O:12])[NH:8][C:7]1=[O:14].C([O-])([O-])=O.[Cs+].[Cs+].[C:22]1([S:28][CH2:29]Cl)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CO.CN(C=O)C>[C:22]1([S:28][CH2:29][N:8]2[C:7](=[O:14])[CH:6]([CH2:5][CH2:4][CH:3]([CH3:15])[CH3:2])[N:10]([CH3:11])[S:9]2(=[O:13])=[O:12])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 81623Chloromethyl phenyl sulphideHCID 867492844-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide cesium salt

生成物 1

HCID 194244062-Phenylthiomethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide収率 70.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
85 °C

実験手順

A mixture of 4-(3-methylbutyl) -5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide cesium salt (prepared by reacting 7.7 g (34.95 retool) of the 1,1-dioxide in methanol with 5 5.13 g of Cs2CO3 followed by removal of the solvent) and phenylthiomethyl chloride (6.65 g, 41.94 mmol) suspended in DMF was heated at 85° C. for 17 hours. The mixture was cooled, and poured into 300 ml of ice/water. The reaction mixture was extracted with ethyl acetate (3×) and the organic layer was washed with water and brine, and dried over sodium sulfate. The organic layer was concentrated in vacuo and the residue was purified by silica column chromatography (10% ethyl acetate in hexane) to afford 8.15 g (70.6%) of 2-phenylthiomethyl-4-(3-methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula VI: R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3) as an oil.

後処理

  1. customprepared
  2. temperatureThe mixture was cooled
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×)
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic layer was concentrated in vacuo
  7. customthe residue was purified by silica column chromatography (10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-bf008be80a844429a208399a98e118ca
出典データセット
uspto-grants-1996_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05494925

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート