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

HRID 1040724노트

반응식

HRID 1040724 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-72684f3825e545929517cf2aa97373cd
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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