1,1'-Carbonyldiimidazole → 5-Chloro-1,3-dihydro-6-nitro-2H-benzimidazol-2-one

HRID 2401488ノート

反応式

HRID 2401488 の反応式
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([NH2:11])=[C:4]([NH2:12])[CH:3]=1.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1>C1COCC1>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]2[NH:11][C:18](=[O:19])[NH:12][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57026184-Chloro-5-nitro-o-phenylenediamine

生成物 1

HCID 145662265-Chloro-1,3-dihydro-6-nitro-2H-benzimidazol-2-one収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A stirred solution of 4-chloro-5-nitro-1,2-phenylenediamine (2.0 g, 10.66 mmol) and CDI (2.59 g, 16 mmol) in anhydrous THF (50 mL) was heated to 85° C. for 4 h. The reaction was allowed to cool and the solvents were removed under reduced pressure. The resulting residue was washed with 2M aqueous hydrochloric acid and recrystallised from methanol to afford 5-chloro-6-nitro-1H-benzo[d]imidazol-2(3H)-one as a brown solid (1.9 g, 84%), which was taken through to the next step with no further purification.

後処理

  1. temperatureto cool
  2. customthe solvents were removed under reduced pressure
  3. washThe resulting residue was washed with 2M aqueous hydrochloric acid
  4. customrecrystallised from methanol

出典と根拠

ORDレコード
ord-e68b6d7080e049eaa3e7dcf43a4664da
出典データセット
uspto-grants-2014_08
特許番号
US08796296B2

反応ノート

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