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Imidazole → methyl 6-(1H-imidazol-1-yl)nicotinate

HRID 1031423
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HRID 1031423 반응식
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.[Na].[H-].[Na+].N1C=CN=C1>CN(C=O)C>[N:12]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)[CH:16]=[CH:15][N:14]=[CH:13]1
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참가 물질

6

반응물 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 57373095Imidazole sodium

생성물 1

HCID 4315458methyl 6-(1H-imidazol-1-yl)nicotinate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
120 °C

실험 절차

A solution of the methyl ester obtained in Step 1. above (16.29 g) in DMF is added dropwise to a DMF suspension of sodium imidazole [prepared from NaH (4.19 g) and imidazole 6.49 g)] at RT. The reaction mixture is heated to 120° C. for nineteen hours. The cooled reaction mixture is partitioned between water and chloroform, the organic layer separated, washed with water, dried over Na2SO4, filtered, evaporated, and residual DMF removed under high vacuum yielding the desired product as a tan solid which is recrystalized from methanol (M.P. 183°-184.5° C.) before use in the next step.

후처리

  1. customThe cooled reaction mixture
  2. customis partitioned between water and chloroform
  3. customthe organic layer separated
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customresidual DMF removed under high vacuum

출처 및 근거

ORD 기록
ord-7a26954fa51e47a0b75f6a3409012ef8
출처 데이터셋
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04954494

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