Nitrogen → 4-[(2,4-Dinitro-phenyl)-methyl-carbamoyl]-butyric acid methyl ester

HRID 1967480Notes

Reaction equation

HRID 1967480 reaction equation
N#N.[CH3:3][O:4][C:5](=[O:24])[CH2:6][CH2:7][CH2:8][C:9](=[O:23])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21].S(OC)(O[CH3:29])(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:3][O:4][C:5](=[O:24])[CH2:6][CH2:7][CH2:8][C:9](=[O:23])[N:10]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21])[CH3:29]

Participants

6

Reactant 4

HCID 947NitrogenHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 866564154-(2,4-Dinitro-phenylcarbamoyl)-butyric acid methyl ester

Product 1

HCID 583828074-[(2,4-Dinitro-phenyl)-methyl-carbamoyl]-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 100 mL round bottom 3-neck flask equipped with stir bar, thermocouple, and N2 sweep were charged 16.67 g (53.6 mmol) of 4-(2,4-dinitro-phenylcarbamoyl)-butyric acid methyl ester and 50 mL (5 volumes vs. dinitroaniline) of acetonitrile at room temperature. To this clear yellow stirred solution was then added 6.09 mL (8.10 g, 64.2 mmol, 1.2 equiv) of dimethyl sulfate and 14.80 g (107 mmol, 2.0 equiv) of K2CO3. The mixture turned dark reddish orange with the addition and exhibited an exotherm of less than 5° C. The reaction was monitored periodically by HPLC Method A and was complete after 22.5 hours at room temperature.

Workup

  1. customTo a 100 mL round bottom 3-neck flask equipped
  2. additionThe mixture turned dark reddish orange with the addition
  3. customan exotherm of less than 5° C

Sources & evidence

ORD record
ord-5c7b67086f164b4292894d365813154f
Source dataset
uspto-grants-2013_04
Patent number
US08420829B2

Reaction notes

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