Sodium Azide → 4-(3-Azido-1-imidazol-1-yl-propyl)-benzonitrile

HRID 1421780ノート

反応式

HRID 1421780 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH2:10][CH2:11]OS(C)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([CH2:11][CH2:10][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)=[N+:23]=[N-:24]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 54062353Methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester

生成物 1

HCID 187797504-(3-Azido-1-imidazol-1-yl-propyl)-benzonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester (600 mg, 2 mmol) was suspended in degassed DMF under argon and sodium azide (650 mg, 10 mmol) was added and the reaction was stirred for 4 hours. The solvent was removed in vacuo and the residue was suspended in ethyl acetate (200 mL) and extracted 2 times with saturated aqueous sodium bicarbonate (100 mL), then water (100 mL), then saturated sodium chloride solution (100 mL). The organic solvent was removed in vacuo and the residue was chromatographed on silica gel eluting with 1:2 ethyl acatate: hexanes. The desired fractions were concentrated in vacuo to give the desired product.

後処理

  1. customThe solvent was removed in vacuo
  2. extractionextracted 2 times with saturated aqueous sodium bicarbonate (100 mL)
  3. customThe organic solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel eluting with 1:2 ethyl acatate
  5. concentrationThe desired fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-377b8db9dccc4020a60c9e2acc6242ae
出典データセット
uspto-grants-2000_06
特許番号
US06077853

反応ノート

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