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

HRID 1421780노트

반응식

HRID 1421780 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-377b8db9dccc4020a60c9e2acc6242ae
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077853

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