Methyl 4-chloroformylbutyrate → 4-[(2,4-Dinitro-phenyl)-methyl-carbamoyl]-butyric acid methyl ester
Reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[CH3:15][O:16][C:17](=[O:24])[CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>>[CH3:15][O:16][C:17](=[O:24])[CH2:18][CH2:19][CH2:20][C:21](=[O:22])[N:2]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:1]Participants
3
Conditions
- Temperature
- 138 °C
Procedure
To a stirred suspension of 1-methylamino-2,4-dinitrobenzene (1.00 g, 5.07 mmol) in xylenes (10 mL) was added methyl-5-chloro-5-oxo-valerate (3.50 mL, 25.28 mmol, 5.0 equiv.) at 20° C. The reaction mixture was then heated to reflux, approximately 138° C. Reaction progress was monitored periodically by HPLC Method A. The reaction was complete after stirring for approximately 24 hours at 138° C. The reaction mixture was cooled to 0° C. and hexanes was added (10 mL) to crystallize the product. The resultant slurry was stirred for approximately 1 hour at −10° C. to 0° C. and then filtered. The wet cake was dried at 60° C. under vacuum/N2 sweep overnight to give 1.30 g (79% yield) as an off-while solid.
Workup
- temperatureThe reaction mixture was then heated
- customReaction progress
- temperatureThe reaction mixture was cooled to 0° C.
- customto crystallize the product
- stirringThe resultant slurry was stirred for approximately 1 hour at −10° C. to 0° C.
- filtrationfiltered
- dry with materialThe wet cake was dried at 60° C. under vacuum/N2
- waitsweep overnight
- customto give 1.30 g (79% yield) as an off-while solid
Sources & evidence
- ORD record
- ord-749aac15b78248ce9e5ca48ac48c6c1c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420829B2
Reaction notes
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