Water → 7-Nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one

HRID 1040724ノート

反応式

HRID 1040724 の反応式
[NH2:1][CH2:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].C1N=CN([C:19](N2C=NC=C2)=[O:20])C=1.O>O1CCCC1>[N+:11]([C:9]1[CH:8]=[CH:7][C:4]2[CH2:5][NH:6][C:19](=[O:20])[NH:1][CH2:2][C:3]=2[CH:10]=1)([O-:13])=[O:12]

参加物

5

反応物 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 224518872-Aminomethyl-4-nitrobenzylamine

生成物 1

HCID 105125087-Nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-aminomethyl-4-nitrobenzylamine (3.10 g, 17.1 mmol) was dissolved in tetrahydrofuran (300 mL) and a solution of N,N-carbonyldiimidazole (2.78 g, 17.1 mmol) in THF (40 mL) was added dropwise at room temperature over 30 minutes. The reaction was allowed to stir at room temperature for 72 hours. The solution was then poured over water (150 mL) and organics were extracted with ethyl acetate (3×100 mL). Combined organic extracts were dried over Na2SO4, filtered and reduced to afford 7-nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one as a crude brown solid. Purification by flash column chromatography (0% MeOH/DCM-10% MeOH/DCM) afforded 2.5 grams of 7-nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one as a yellow solid. LC/MS (ESI)=208.42 (M+H).

後処理

  1. extractionorganics were extracted with ethyl acetate (3×100 mL)
  2. dry with materialCombined organic extracts were dried over Na2SO4
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-72684f3825e545929517cf2aa97373cd
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

反応ノート

読み込み中…