Sodium Azide → HCID 178497409、化合物

HRID 343529ノート

反応式

HRID 343529 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 178497409HCID 178497409、化合物

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2b94506ad7804d7c8ba67a127f5f4e11
出典データセット
uspto-grants-1999_01
特許番号
US05861417

反応ノート

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