Phosgene → 4-(5-Bromo-2-pyrimidinyloxy)-3-chlorophenylisocyanate

HRID 4515ノート

反応式

HRID 4515 の反応式
[C:1](Cl)(Cl)=[O:2].[Br:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[Cl:20])=[N:10][CH:11]=1>C(OCC)(=O)C>[Br:5][C:6]1[CH:11]=[N:10][C:9]([O:12][C:13]2[CH:19]=[CH:18][C:16]([N:17]=[C:1]=[O:2])=[CH:15][C:14]=2[Cl:20])=[N:8][CH:7]=1

参加物

4

反応物 2

HCID 6371PhosgeneHCID 137714404-(5-Bromo-2-pyrimidinyloxy)-3-chloroaniline

生成物 1

HCID 102458504-(5-Bromo-2-pyrimidinyloxy)-3-chlorophenylisocyanate収率 95.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒3 回

実験手順

Into a flask, a solution of 0.02 mol of phosgene in 30 ml of ethyl acetate was introduced. To this solution, a solution of 3 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline in 10 ml of ethyl acetate was dropwise added at room temperature. The mixture was reacted at room temperature for 3 hours under stirring and further under reflux for one hour. After completion of the reaction, ethyl acetate was distilled off under reduced pressure, and the residue was vacuum-dried to obtain 3.10 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chlorophenylisocyanate having a melting point of from 63 to 68° C. (2) Into a flask, 1.22 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chlorophenylisocyanate obtained in the above step was introduced, and 20 ml of toluene was added thereto. Further, 0.62 g of 2-nitrobenzamide was added under stirring. The mixture was reacted under reflux for 4 hours. After completion of the reaction, 5 ml of methanol was added to the reaction product, and the mixture was cooled. The precipitated crystals were collected by filtration to obtain 0.79 g of the desired product.

後処理

  1. customThe mixture was reacted at room temperature for 3 hours
  2. temperaturefurther under reflux for one hour
  3. distillationwas distilled off under reduced pressure
  4. customthe residue was vacuum-dried

出典と根拠

ORDレコード
ord-7ff718f3b7e94c629eff1d63f4573f1b
出典データセット
uspto-grants-1988_02
特許番号
US04727077

反応ノート

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