Sodium Azide → HCID 178497409, 화합물

HRID 343529노트

반응식

HRID 343529 반응식
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[N-:15]=[N+:16]=[N-:17].[Na+].Cl.C([NH+](CC)CC)C>CN1CCCC1=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([C:13]2[NH:17][N:16]=[N:15][N:14]=2)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

참가 물질

5

반응물 3

HCID 33557Sodium AzideHCID 18464789Methyl 5-cyano-2-methoxybenzoateHCID 21900368Triethylammonium hydrochloride

생성물 1

HCID 178497409HCID 178497409, 화합물

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
150 °C

실험 절차

Combine methyl 2-methoxy-5-cyanobenzoate (0.67 mmol), sodium azide (0.13 g, 2.04 mmol), and triethylammonium hydrochloride (0.14 g, 1.03 mmol) in N-methylpyrrolidinone (6 mL). Heat to 150° C. After 4 hours, cool to ambient temperature and partition the reaction mixture between water and ethyl acetate. Separate the layers and extract the aqueous layer three times with ethyl acetate. Adjust the pH of the aqueous layer to about 1 using a 1M aqueous hydrochloric acid solution. The aqueous layer is again extracted three times with ethyl acetate, and twice with dichloromethane. The aqueous layer is saturated with sodium chloride and again extracted four times with dichloromethane. Combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give methyl 2-methoxy-5-(1H-tetrazol-5-yl)benzoate.

후처리

  1. temperaturecool to ambient temperature
  2. custompartition the reaction mixture between water and ethyl acetate
  3. customSeparate the layers
  4. extractionextract the aqueous layer three times with ethyl acetate
  5. extractionThe aqueous layer is again extracted three times with ethyl acetate
  6. extractionagain extracted four times with dichloromethane
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-2b94506ad7804d7c8ba67a127f5f4e11
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05861417

반응 노트

불러오는 중…