Urea → 2H-Benzimidazol-2-one, 5-chloro-1,3-dihydro-1-(1-methylethyl)-

HRID 1654476ノート

反応式

HRID 1654476 の反応式
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[NH:4][CH:5]([CH3:7])[CH3:6].N[C:14](N)=[O:15]>O>[Cl:12][C:10]1[CH:9]=[CH:8][C:3]2[N:4]([CH:5]([CH3:7])[CH3:6])[C:14](=[O:15])[NH:1][C:2]=2[CH:11]=1

参加物

4

反応物 2

HCID 1176UreaHCID 27357454-Chloro-N~1~-(propan-2-yl)benzene-1,2-diamine

生成物 1

HCID 108461602H-Benzimidazol-2-one, 5-chloro-1,3-dihydro-1-(1-methylethyl)-収率 43.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

A mixture of 2-amino-4-chloro-N-isopropylaniline (14 g) and urea (15 g) was stirred at 160° C. for 3.5 hours. After cooling, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with diluted hydrochloric acid, an aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. To the residue was added isopropyl alcohol and the obtained crystal was separated by filtration and recrystallized from acetonitrile to give 5-chloro-1-isopropylbenzimidazol-2-one (7 g).

後処理

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with diluted hydrochloric acid
  4. dry with materialan aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo the residue was added isopropyl alcohol
  7. customthe obtained crystal was separated by filtration
  8. customrecrystallized from acetonitrile

出典と根拠

ORDレコード
ord-0ffd5348313c483d8daac2673a2bbd66
出典データセット
uspto-grants-1995_04
特許番号
US05407936

反応ノート

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