Pyridine → {[1-(naphthalen-1-yl)-1H-tetrazol-5-yl]sulfanyl}acetic acid

HRID 1988796

反応式

HRID 1988796 の反応式
N1C=CC=CC=1.[C:7]1([N:17]2[C:21](=[S:22])[N:20]=[N:19][NH:18]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.Br[CH2:24][C:25]([O:27]C)=[O:26]>CS(C)=O.CCOC(C)=O>[C:7]1([N:17]2[C:21]([S:22][CH2:24][C:25]([OH:27])=[O:26])=[N:20][N:19]=[N:18]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 60984Methyl bromoacetateHCID 27317011,2-Dihydro-1-naphthyl-5H-tetrazole-5-thione

生成物 1

HCID 29070259{[1-(naphthalen-1-yl)-1H-tetrazol-5-yl]sulfanyl}acetic acid収率 92.3%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Pyridine (0.83 mL, 10.3 mmol) and 1,2-dihydro-1-(1-naphthalenyl)-5H-tetrazole-5-thione (2.14 g, 9.38 mmol) were added to a solution of methyl 2-bromoacetate (977 μL, 10.3 mmol) in DMSO (50 mL). The resulting light yellow solution was stirred at room temperature for 2 h. The reaction mixture was then diluted with EtOAc (300 ml) and was successively washed with water (2×250 ml) and brine (100 ml), dried (MgSO4), filtered and concentrated under reduced pressure. The crude ester was dissolved in THF and aqueous 1 N NaOH solution was added. The solution was stirred at room temperature for 30 min. The THF was evaporated under reduced pressure and the residue was dissolved in aqueous 1 N NaOH solution. The solution was slowly acidified to pH 2 at 0° C. with aqueous 1 N HCl solution. The suspension was filtered and the resulting solid was rinsed with water and dried under reduced pressure to give the title compound (2.48 g, 92% yield) as a white solid.

後処理

  1. washwas successively washed with water (2×250 ml) and brine (100 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe crude ester was dissolved in THF
  6. additionaqueous 1 N NaOH solution was added
  7. stirringThe solution was stirred at room temperature for 30 min
  8. customThe THF was evaporated under reduced pressure
  9. dissolutionthe residue was dissolved in aqueous 1 N NaOH solution
  10. customwas slowly acidified to pH 2 at 0° C. with aqueous 1 N HCl solution
  11. filtrationThe suspension was filtered
  12. washthe resulting solid was rinsed with water
  13. customdried under reduced pressure

出典と根拠

ORDレコード
ord-35c8c0f67b7241feb41bc2376819755a
出典データセット
uspto-grants-2010_01
特許番号
US07642277B2

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