Hydrochloric Acid → 1,2-Dihydro-1-naphthyl-5H-tetrazole-5-thione

HRID 1988795

반응식

HRID 1988795 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]1([N:15]=[C:16]=[S:17])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.Cl>O1CCOCC1.O>[C:5]1([N:15]2[C:16](=[S:17])[N:1]=[N:2][NH:3]2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 110801-Naphthyl IsothiocyanateHCID 33557Sodium Azide

생성물 1

HCID 27317011,2-Dihydro-1-naphthyl-5H-tetrazole-5-thione수율 63.1%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
102 °C

실험 절차

To a solution of NaN3 (1.76 g, 27.0 mmol) in a mixture of 1,4-dioxane (25 mL) and water (25 mL) was added 1-naphthalenylisothiocyanate (5.00 g, 27.0 mmol) at room temperature. The yellow solution containing a white solid was heated at 102° C. for 2 h. The reaction mixture was then cooled to room temperature and aqueous 1 N HCl solution was added until pH 2 was reached. The aqueous mixture was extracted with EtOAc (250 mL). The organic layer was extracted with aqueous 1 N NaOH solution. The aqueous layer was acidified with aqueous 6 N HCl solution and a white precipitate formed. The suspension was filtered and the resulting solid was triturated with Et2O/hexane (1/1) to give the title compound (3.89 g, 63% yield) as an off white solid.

후처리

  1. additionThe yellow solution containing a white solid
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. extractionThe aqueous mixture was extracted with EtOAc (250 mL)
  4. extractionThe organic layer was extracted with aqueous 1 N NaOH solution
  5. customa white precipitate formed
  6. filtrationThe suspension was filtered
  7. customthe resulting solid was triturated with Et2O/hexane (1/1)

출처 및 근거

ORD 기록
ord-7411681d06e64eef985d0f190b753462
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642277B2

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