Triethylamine → (E)-1-cinnamyl-3-(3-pyridyl)imidazolidine-2-thione

HRID 477001ノート

反応式

HRID 477001 の反応式
[CH2:1]([NH:10][CH2:11][CH2:12][NH:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:27](Cl)(Cl)=[S:28]>O1CCCC1>[CH2:1]([N:10]1[CH2:11][CH2:12][N:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C:27]1=[S:28])/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 14834214(E)-N-cinnamyl-N'-(3-pyridyl)ethylenediamine

生成物 1

HCID 14834215(E)-1-cinnamyl-3-(3-pyridyl)imidazolidine-2-thione収率 45.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 5.37 g of (E)-N-cinnamyl-N'-(3-pyridyl)ethylenediamine dissolved in 100 ml of tetrahydrofuran, 4.5 g of triethylamine was added and the mixture was ice-cooled. To the mixture was added dropwise 20 ml of a tetrahydrofuran solution containing 5.12 g of thiophosgene over 5 minutes, and subsequently the mixture was stirred under ice-cooling for 30 minutes and then at room temperature for 2 hours. The solvent was distilled off, and the residue was dissolved in chloroform, washed with water and dried, followed by distillation of the solvent. The residue was purified by silica gel column chromatorgraphy (solvent: chloroform-methanol=20:1) to give 2.86 g of (E)-1-cinnamyl-3-(3-pyridyl)imidazolidine-2-thione as caramel.

後処理

  1. temperaturecooled
  2. temperaturecooling for 30 minutes
  3. distillationThe solvent was distilled off
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with water
  6. customdried
  7. distillationfollowed by distillation of the solvent
  8. customThe residue was purified by silica gel column chromatorgraphy (solvent: chloroform-methanol=20:1)

出典と根拠

ORDレコード
ord-4e1d32d67184480d8caeb5e852673a2b
出典データセット
uspto-grants-1989_12
特許番号
US04886817

反応ノート

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