P-Phenylenediamine → N-(4-chloro-3-(trifluoromethyl)phenyl)-N'-(4-aminophenyl)urea

HRID 78329

反応式

HRID 78329 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH:15]1[C:20]([NH2:21])=[CH:19][CH:18]=[C:17]([NH2:22])[CH:16]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:21][C:20]2[CH:15]=[CH:16][C:17]([NH2:22])=[CH:18][CH:19]=2)=[O:10])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

参加物

4

反応物 2

HCID 7814P-PhenylenediamineHCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzene

生成物 1

HCID 23614594N-(4-chloro-3-(trifluoromethyl)phenyl)-N'-(4-aminophenyl)urea収率 97.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 4-chloro-3-(trifluoromethyl)phenyl isocyanate (2.27 g, 10.3 mmol) in CH2Cl2 (308 mL) was added p-phenylenediamine (3.32 g, 30.7 mmol) in one part. The resulting mixture was stirred at room temp. for 1 h, treated with CH2Cl2 (100 mL), and concentrated under reduced pressure. The resulting pink solids were dissolved in a mixture of EtOAc (110 mL) and MeOH (15 mL), and the clear solution was washed with a 0.05 N HCl solution. The organic layer was concentrated under reduced pressure to afford impure N-(4-chloro-3-(trifluoromethyl)phenyl)-N′-(4-aminophenyl)urea (3.3 g): TLC (100% EtOAc) Rf 0.72.

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting pink solids were dissolved in a mixture of EtOAc (110 mL) and MeOH (15 mL)
  3. washthe clear solution was washed with a 0.05 N HCl solution
  4. concentrationThe organic layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-1d4590b940d34104bce128bf5fcbbd34
出典データセット
uspto-grants-2014_09
特許番号
US08841330B2

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