Oxalyl chloride → HCID 44203076, compound
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[NH2:20][CH2:21][C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23].C(N(C(C)C)CC)(C)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH:20][CH2:21][C:22](=[O:23])[NH:24][CH:25]([CH3:27])[CH3:26])=[O:9]Participants
Procedure
To a solution of 5-fluoro-2-nitrobenzoic acid (2.3 g, 12.4 mmol) in dichloromethane (20 mL) was added oxalyl chloride (3.2 g, 2.2 mL, 24.8 mmol) dropwise. After 1 h the solution was concentrated to dryness. 2-Amino-N-isopropylacetamide (INTERMEDIATE I.1) (0.30 g, 2.6 mmol) was dissolved in dichloromethane (20 mL) and diisopropylethylamine (DIEA) (6.8 mL, 38.9 mmol) added. The acid chloride in dichloromethane (10 mL) was added dropwise and the reaction mixture stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo, the residue dissolved in dichloromethane and washed with 1 N NaOH (aq.), 1 N HCl (aq.) and brine. The organic layers were dried (MgSO4) and concentrated in vacuo to yield 5-fluoro-N-(isopropylcarbamoylmethyl)-2-nitrobenzamide (2.7 g, 9.5 mmol, 81%) as a yellow solid.
Workup
- concentrationAfter 1 h the solution was concentrated to dryness
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutionthe residue dissolved in dichloromethane
- washwashed with 1 N NaOH (aq.), 1 N HCl (aq.) and brine
- dry with materialThe organic layers were dried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-37d8fff495794000bc6c90810a8e2a40
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807686B2
Reaction notes
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