Epichlorohydrin → 1-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole

HRID 1895826

反応式

HRID 1895826 の反応式
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15]([CH:17]1[O:19][CH2:18]1)[Cl:16]>>[N+:1]([C:4]1[N:5]([CH2:18][CH:17]([OH:19])[CH2:15][Cl:16])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

参加物

4

反応物 3

HCID 7835EpichlorohydrinHCID 107012-Nitroimidazole2 回HCID 11430Potassium Carbonate

生成物 1

HCID 1145421-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole

実験手順

Epichlorohydrin (100 mL) was added to a mixture of 2-nitroimidazole (11.3 g, 0.1 mol) and 1 g of potassium carbonate and the solution refluxed for 15-20 min until all 2-nitroimidazole was dissolved. The hot solution was filtered and the yellow crystal was collected to give compound (5, 17 g, 83%). 1H NMR (DMSO-d6, δppm): 3.61 (m, 2H, Cl—CH2—), 4.06 (m, 1H, HO—CH—), 4.32 (dd, 1H, N—CHa—, J=13.8 Hz, 8.4 Hz), 4.63 (dd, 1H, N—CHb—, J=13.8 Hz, 3.6 Hz), 5.67 (d, 1H, OH, J=5.7 Hz), 7.15 (s, 1H, —CH═), 7.56 (s, 1H, —CH═). 13C NMR (DMSO-d6, δppm):46.81, 52.27, 68.75, 127.40, 128.45, 144.98.

後処理

  1. dissolutionwas dissolved
  2. filtrationThe hot solution was filtered
  3. customthe yellow crystal was collected
  4. customto give compound (5, 17 g, 83%)

出典と根拠

ORDレコード
ord-c596b35ea0304edd9cc9f66269aefcba
出典データセット
uspto-grants-2013_08
特許番号
US08518371B2

関連ノート

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