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Diphosgene → 5,5-Dimethyl-3-(3-nitro-4-isopropylphenyl)-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione

HRID 2356940
ノート
印刷プレビュー

反応式

HRID 2356940 の反応式
[O:1]=[C:2](Cl)OC(Cl)(Cl)Cl.[N+:9]([C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[CH:19]([CH3:21])[CH3:20])[NH2:15])([O-:11])=[O:10].CO[C:24](=[O:36])[C:25]([CH3:35])([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH3:26]>ClCCCl.C1COCC1>[CH3:35][C:25]1([CH3:26])[N:27]([CH2:28][C:29]2[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=2)[C:2](=[O:1])[N:15]([C:14]2[CH:16]=[CH:17][C:18]([CH:19]([CH3:21])[CH3:20])=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=2)[C:24]1=[O:36]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10426DiphosgeneHCID 221118273-Nitro-4-(propan-2-yl)anilineHCID 43725938HCID 43725938、化合物

生成物 1

HCID 116609365,5-Dimethyl-3-(3-nitro-4-isopropylphenyl)-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒2 回
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
50 °C

実験手順

6.04 g (30 mmol) diphosgene in 50 ml 1,2-dichlorethane were treated at −20° C. with a solution of 2 g (11.1 mmol) 3-nitro-4-isopropyl-aniline in 20 ml 1,2-dichlorethane. The mixture was allowed to come to room temperature and then was heated to 50° C. for 5 h. After standing over night, the solvent was evaporated and the residual oil was taken up in 40 ml THF. 3.93 g (18.7 mmol) 2-methyl-2-[(pyridin-4-ylmethyl)-amino]-propionic acid methyl ester in 30 ml THF were added and the mixture was refluxed for 6 h. The solvent was evaporated and the residue taken up in ethylacetate and washed with water. THe organic phase was dried, the solvent evaporated and the residue was purified by preparative HPLC. (C18 reversed phase column, elution with a water (0.1% trifluoracetic acid)/acetonitrile gradient) Yield: 2.7 g.

後処理

  1. customto come to room temperature
  2. waitAfter standing over night
  3. customthe solvent was evaporated
  4. temperaturethe mixture was refluxed for 6 h
  5. customThe solvent was evaporated
  6. washwashed with water
  7. customTHe organic phase was dried
  8. customthe solvent evaporated
  9. customthe residue was purified by preparative HPLC
  10. washphase column, elution with a water (0.1% trifluoracetic acid)/acetonitrile gradient) Yield: 2.7 g

出典と根拠

ORDレコード
ord-58f96f2b67504f08a9f6457e9921f285
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07759379B2

反応ノート

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