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Dimethyl Disulfide → Methyl 4,7-dimethyl-3-methylsulfenylindole-2-carboxylate

HRID 361623
ノート
印刷プレビュー

反応式

HRID 361623 の反応式
CS[S:3][CH3:4].S(Cl)(Cl)(=O)=O.[CH3:10][C:11]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]2[C:12]=1[CH:13]=[C:14]([C:21]([O:23][CH3:24])=[O:22])[NH:15]2>ClCCCl.CN(C=O)C.C(OCC)(=O)C>[CH3:10][C:11]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]2[C:12]=1[C:13]([S:3][CH3:4])=[C:14]([C:21]([O:23][CH3:24])=[O:22])[NH:15]2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 12232Dimethyl DisulfideHCID 24648Sulfuryl chlorideHCID 4714976methyl 4,7-dimethyl-1H-indole-2-carboxylate

生成物 1

HCID 53833292Methyl 4,7-dimethyl-3-methylsulfenylindole-2-carboxylate収率 105.1%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Under ice-cooling, 0.89 ml (7.4 mmol) of dimethyl disulfide was dissolved in 20 ml of 1,2-dichloroethane, and 0.53 ml (6.5 mmol) of sulfuryl chloride was added. The reaction mixture was stirred for 20 minutes and a solution of 2.00 g (9.8 imnol) of methyl 4,7-dimethylindole-2-carboxylate in 10 ml of anhydrous DMF was added. The reaction mixture was stirred for 2 hours, then dissolved in ethyl acetate and washed with water. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide 1.94 g of white crystals. Yield: 80%

後処理

  1. temperatureUnder ice-cooling
  2. stirringThe reaction mixture was stirred for 2 hours
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-5ecd86f17f7a45298e3846f5b76a82a7
出典データセット
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05866594

反応ノート

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