Pyridine → 4-Chloro-N-(4-chloropyrimidin-5-yl)-3-cyanobenzamide

HRID 1877750ノート

反応式

HRID 1877750 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]#[N:12].S(Cl)(Cl)=O.[NH2:17][C:18]1[C:19]([Cl:24])=[N:20][CH:21]=[N:22][CH:23]=1.N1C=CC=CC=1>C1C=CC=CC=1.O.C(Cl)(Cl)Cl.ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:17][C:18]2[C:19]([Cl:24])=[N:20][CH:21]=[N:22][CH:23]=2)=[O:8])=[CH:4][C:3]=1[C:11]#[N:12]

参加物

9

反応物 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 134045414-Chloropyrimidin-5-amineHCID 226446124-Chloro-3-cyanobenzoic acid

生成物 1

HCID 714261974-Chloro-N-(4-chloropyrimidin-5-yl)-3-cyanobenzamide収率 65%

試薬・触媒・溶媒 4

HCID 241Benzene溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Chloro-3-cyanobenzoic acid (7.01 g, 38.6 mmol) was suspended in benzene (70 mL). Thionyl chloride (3.6 mL, 49.6 mmol) was added to the suspension, and the mixture was refluxed with heating for 4 hours. The reaction liquid was condensed under reduced pressure. 5-Amino-4-chloropyrimidine (5.00 g, 38.6 mmol), dichloromethane (70 mL), and pyridine (3.6 mL, 44.5 mmol) were added to the obtained acid chloride. The mixture was stirred at room temperature for 7 hours. Chloroform (50 mL) and water (50 mL) was added to the reaction solution to filtrate crystals. The obtained crystals were washed with chloroform (20 mL) and water (20 mL), and air-dried to obtain 7.35 g (yield: 65%) of the subject compound as white crystals. Further, 0.62 g (yield: 8%) of the subject compound was obtained from a mixed solution of mother liquid and washings as pale brown crystals (secondary crystals). The total yield was 73%.

後処理

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 4 hours
  3. customThe reaction liquid
  4. customcondensed under reduced pressure
  5. washThe obtained crystals were washed with chloroform (20 mL) and water (20 mL)
  6. customair-dried

出典と根拠

ORDレコード
ord-62a4a92b051e418388ead2567e3ea4a2
出典データセット
uspto-grants-2012_11
特許番号
US08314085B2

反応ノート

読み込み中…