Hydrochloric Acid → 2-[1-(2-chloro-3-ethynyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole

HRID 1254974ノート

反応式

HRID 1254974 の反応式
[CH2:1]([NH2:4])[CH2:2][NH2:3].CO[C:7](=N)[CH:8]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[CH:19])[C:13]=1[Cl:20])[CH2:9][CH3:10].Cl>C(O)C>[Cl:20][C:13]1[C:14]([C:18]#[CH:19])=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][CH:8]([C:7]1[NH:3][CH2:2][CH2:1][N:4]=1)[CH2:9][CH3:10]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 595657822-(2-Chloro-3-ethynyl-phenoxy)-butyrimidic acid methyl ester

生成物 1

HCID 595657832-[1-(2-chloro-3-ethynyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

反応条件

温度
0 °C

実験手順

Ethylene diamine (30 mg, 0.5 mmol) was dissolved in dry ethanol (1.9 ml). The solution was cooled to 0° C. and 2-(2-chloro-3-ethynyl-phenoxy)-butyrimidic acid methyl ester (100 mg, 0.4 mmol) was added. After 1 h a solution of concentrated HCl (few drops) in ethanol (0.9 ml) was added and the reaction mixture was stored overnight at 0° C. The reaction mixture was then diluted with a further portion of ethanol (1.6 ml) and heated to 75° C. for 5 h. After cooling to room temperature a precipitate was formed that was filtered and discarded. The filtrate was evaporated and treated with CHCl3. Another precipitate was formed, which was filtered again. Finally, the CHCl3 phase was evaporated to yield 2-[1-(2-chloro-3-ethynyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole; 1H-NMR (CDCl3) 1.08 t, 3H, 1.9-2.1 m, 2H, 3.10-3.9, vbr s, 4H, 3.39, s, 1H, 4.85 dd, 1H, 7.05 d, 1H, 7.1-7.2, m, 2H.

後処理

  1. temperatureheated to 75° C. for 5 h
  2. temperatureAfter cooling to room temperature a precipitate
  3. customwas formed
  4. filtrationthat was filtered
  5. customThe filtrate was evaporated
  6. additiontreated with CHCl3
  7. customAnother precipitate was formed
  8. filtrationwhich was filtered again
  9. customFinally, the CHCl3 phase was evaporated

出典と根拠

ORDレコード
ord-324c5c8a89c442fa8a9e43fa85c8e203
出典データセット
uspto-grants-2013_06
特許番号
US08455663B2

反応ノート

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