Sodium ethoxide → 8-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68939Notes

Reaction equation

HRID 68939 reaction equation
[O-]CC.[Na+].C([O:7][C:8](=O)[CH2:9][C:10]([N:12]([C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[NH2:22])[CH3:13])=[O:11])C>C(O)C>[CH3:21][O:20][C:18]1[CH:17]=[CH:16][C:15]2[NH:22][C:8](=[O:7])[CH2:9][C:10](=[O:11])[N:12]([CH3:13])[C:14]=2[CH:19]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 66961118N-(2-amino-5-methoxyphenyl)-N-methylmalonamic acid ethyl ester

Product 1

HCID 669610818-Methoxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

Sodium ethoxide (204 mg) was added to an ethanol solution (15 ml) of N-(2-amino-5-methoxyphenyl)-N-methylmalonamic acid ethyl ester (266 mg). The mixture was stirred at 65° C. for 2.5 hours. The reaction liquid was cooled to room temperature, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=1:0→10:1). The purified product was condensed to dryness under reduced pressure to give the title compound (176.3 mg) as a white powder.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. customcondensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=1:0→10:1)
  5. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-5d80f3da5efe4a8a85c3919cd7c4e1ed
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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