Cyclopentylamine → N-(2-Chloro-4-pyridinyl)-N′-cyclopentylurea

HRID 619877ノート

反応式

HRID 619877 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:17])OC2C=CC=CC=2)[CH:5]=[CH:4][N:3]=1.[CH:18]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19]1>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([NH:23][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:5]=[CH:4][N:3]=1

参加物

4

反応物 2

HCID 2906CyclopentylamineHCID 21247422Phenyl (2-chloropyridin-4-yl)carbamate

生成物 1

HCID 14625237N-(2-Chloro-4-pyridinyl)-N′-cyclopentylurea収率 85.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A stirred solution of 3.5 grams (0.0141 mole) of phenyl N-(2-chloro-4-pyridinyl)carbamate and 1.7 ml (0.0172 mole) of cyclopentylamine in 60 ml of acetone was heated under reflux for three hours. The reaction mixture was cooled and concentrated under reduced pressure to a residual oil. The oil was dissolved in 20 ml of methylene chloride and passed through a column of silica gel. Elution was accomplished with 5% and 10% acetone-methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure to yield 2.9 grams of N-(2-chloro-4-pyridinyl)-N'-cyclopentylurea; m.p. 119°-121° C. The nmr spectrum was consistent with the proposed structure.

後処理

  1. temperatureunder reflux for three hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure to a residual oil
  4. dissolutionThe oil was dissolved in 20 ml of methylene chloride
  5. washElution
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3dad35d76aeb4b838342935cc8eec840
出典データセット
uspto-grants-1989_04
特許番号
US04818271

反応ノート

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