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

HRID 1687032Notes

Reaction equation

HRID 1687032 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-a7200a21c6b2441f98d53904e3677826
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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