alpha-Chloro-m-nitrotoluene → 9-(3-Nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 361562Notes

Reaction equation

HRID 361562 reaction equation
[CH2:1]1[CH:10]2[C:4](=[N:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9]2=[O:11])[CH2:3][CH2:2]1.[H-].[Na+].[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Cl)([O-:20])=[O:19]>CN(C=O)C.[Cl-].[NH4+]>[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][N:8]1[C:9](=[O:11])[CH:10]2[CH2:1][CH2:2][CH2:3][C:4]2=[N:5][C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]1=2)([O-:20])=[O:19]

Participants

6

Reactant 3

HCID 12078alpha-Chloro-m-nitrotolueneHCID 24758Sodium hydrideHCID 123949352,3,9,10a-Tetrahydro-1H-benzo[b]cyclopenta[f][1,4]diazepin-10-one

Product 1

HCID 701126829-(3-Nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneYield 71.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (4.00 g, 20 mmol) in DMF (40 mL) was cooled to 0° C. and sodium hydride (a 60% dispersion in liquid paraffin, 0.80 g, 20 mmol) was added. This mixture was stirred at the same temperature for 20 minutes. To the resulting solution was added 3-nitrobenzyl chloride (3.77 g, 22 mmol) and the mixture was stirred at room temperature for 20 minutes. This reaction mixture was poured in saturated aqueous ammonium chloride solution (40 mL) and extracted with 3 portions of ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-diisopropyl ether to provide 4.81 g (yield 71%) of the title compound. m.p. 123.5°-125.5° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 minutes
  2. extractionextracted with 3 portions of ethyl acetate
  3. washThe pooled organic layer was washed with water and saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-7b18bcc2161348e0b020f64ca5116cb6
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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