Sulfuric Acid → 2-(2-Tosylethylthio)nicotinic acid

HRID 660051

反応式

HRID 660051 の反応式
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11]1([CH3:23])[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH2:21]O)(=[O:19])=[O:18])=[CH:13][CH:12]=1.OS(O)(=O)=O>CN(C=O)C>[S:17]([CH2:20][CH2:21][S:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([C:14]1[CH:15]=[CH:16][C:11]([CH3:23])=[CH:12][CH:13]=1)(=[O:19])=[O:18]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 89682Ethanol, 2-[(4-methylphenyl)sulfonyl]-HCID 178524460HCID 178524460、化合物

生成物 1

HCID 687267972-(2-Tosylethylthio)nicotinic acid収率 14.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 7.3 g (47 mmol) of 2-mercaptonicotinic acid and 9.6 g (48 mmol) of 2-(p-toluenesulfonyl)-ethanol was dissolved in DMF (80 ml). 0.5 ml of conc. H2SO4 was then carefully added dropwise, and stirring was carried out overnight under reflux. The reaction mixture was concentrated using a Genevac (EZ2). The residue was dissolved in acetonitrile and the solid was separated off. The mother liquor was concentrated, and MeOH was added. The resulting solid was filtered off and dried. 2.35 g (7 mmol, 14.8%) of 2-(2-tosylethylthio)nicotinic acid were obtained as solid.

後処理

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in acetonitrile
  4. customthe solid was separated off
  5. concentrationThe mother liquor was concentrated
  6. additionMeOH was added
  7. filtrationThe resulting solid was filtered off
  8. customdried

出典と根拠

ORDレコード
ord-11d018d06d50488199d2b9b4a624a474
出典データセット
uspto-grants-2011_12
特許番号
US08084470B2

関連ノート

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