Triethylamine → N-cyano-N'-(4-dimethylaminobenzyl)-3-pyridinecarboximidamide

HRID 374151ノート

反応式

HRID 374151 の反応式
[C:1]([N:3]=[C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)OC(C)C)#[N:2].Cl.Cl.[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.C(N(CC)CC)C>CO>[C:1]([NH:3][C:4]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[N:24][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([N:18]([CH3:27])[CH3:17])=[CH:20][CH:21]=1)#[N:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochlorideHCID 100812013-Pyridinecarboximidic acid, N-cyano-, 1-methylethyl ester

生成物 1

HCID 19734510N-cyano-N'-(4-dimethylaminobenzyl)-3-pyridinecarboximidamide収率 88.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Isopropyl N-cyano-3-pyridinecarboximidate (0.50 g, 2.6 mmol) was dissolved in methanol (5 ml), and a solution of p-(dimethylamino)benzylamine dihydrochloride (0.65 g, 2.9 mmol) and triethylamine (0.64 g, 6.4 mmol) in methanol (5 ml) were added. The mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the concentrated residue thus obtained was extracted with ethyl acetate (50 ml×3). The ethyl acetate layer was washed with water (50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual concentrate thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C-200, 30 g) eluting with chloroformmethanol (100:1). The eluted fractions were concentrated under reduced pressure and then crystallized from methanol-diethyl ether to give the title compound (0.63 g, 2.3 mmol, yield: 85%) as colorless powder.

後処理

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe concentrated residue thus obtained
  3. extractionwas extracted with ethyl acetate (50 ml×3)
  4. washThe ethyl acetate layer was washed with water (50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe residual concentrate thus
  8. customobtained
  9. washeluting with chloroformmethanol (100:1)
  10. concentrationThe eluted fractions were concentrated under reduced pressure
  11. customcrystallized from methanol-diethyl ether

出典と根拠

ORDレコード
ord-8a47678b1795405b8b298b63ba7e6e3e
出典データセット
uspto-grants-1992_11
特許番号
US05166347

反応ノート

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