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

HRID 660051노트

반응식

HRID 660051 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 687267972-(2-Tosylethylthio)nicotinic acid수율 14.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-11d018d06d50488199d2b9b4a624a474
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084470B2

반응 노트

불러오는 중…