Pivaloyl chloride → HCID 11506746, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH3:9][C:10]([CH3:15])([CH3:14])[C:11](Cl)=[O:12]>C(Cl)Cl>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:11](=[O:12])[C:10]([CH3:15])([CH3:14])[CH3:9])=[N:3][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
TEA (6.78 mL, 48.6 mmol) was added to a suspension of 2-amino-5-chloropyridine (5.00 g, 38.9 mmol) in DCM (75 mL). The resulting solution was cooled to 0° C. and a solution of 2,2-dimethylpropanoyl chloride (5.74 mL, 46.7 mmol) in DCM (10.0 mL) was added dropwise over a 5 min period. The resulting mixture was allowed to stir at rt for 1 h. The reaction mixture was then transferred to a separatory funnel and washed with a saturated aqueous solution of NaHCO3. The organic solution was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-(5-chloropyridin-2-yl)-2,2-dimethylpropanamide (8.0 g, 40 mmol, 99%). LCMS (FA): m/z=215.1 (M+H).
Workup
- customThe reaction mixture was then transferred to a separatory funnel
- washwashed with a saturated aqueous solution of NaHCO3
- dry with materialThe organic solution was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-27df25c1db514a35ab48fa368488f9af
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268992B2
Reaction notes
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