Ethanolamine → 4-chloro-N-(2-hydroxyethyl)-3-nitrobenzamide
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14]([CH2:16][NH2:17])[OH:15].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:17][CH2:16][CH2:14][OH:15])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a chilled solution (−10° C.) of 4-chloro-3-nitrobenzoyl chloride (1.85 g, 8.4 mmol) in anhydrous THF (60 mL) was added dropwise a solution of ethanolamine (0.48 mL, 8.0 mmol) in THF (20 mL) followed by TEA (1.1 mL, 8.0 mmol). After stirring 1 h while temperature was maintained at −10° C., the solution was combined with a 1:1 mixture of ice and satd NaHCO3 (100 mL) and then extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to give 4-chloro-N-(2-hydroxyethyl)-3-nitrobenzamide (1.74 g, 89%) as a white solid, which was used without purification. TLC (3:22 MeOH/DCM Rf 0.36).
Workup
- extractionextracted with EtOAc (3×100 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-06925e7e35aa4f3dbb60c223e7fe04a1
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696473B2
Reaction notes
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