Diethylcarbamoyl chloride → 6-(Propan-2-yl)pyridine-2-carbonitrile
Reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N+:11]=1[O-])([CH3:9])[CH3:8].C(N(CC)C(Cl)=O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH:7]([C:10]1[N:11]=[C:12]([C:5]#[N:6])[CH:13]=[CH:14][CH:15]=1)([CH3:9])[CH3:8]Participants
Procedure
Trimethylsilyl cyanide (1.53 mL) was added to a solution of 2-isopropylpyridine 1-oxide (example 85, step b) (1.3 g) in DCM (40 mL) and the resulting mixture was stirred for 5 min. Diethylcarbamoyl chloride (1.2 mL) was added and the mixture stirred for 3 days. An aqueous solution of potassium carbonate (10%, 40 mL) was added and the mixture stirred for 10 min. The layers were separated and the aqueous phase extracted with DCM (2×40 mL). The combined organic solutions were washed with brine (40 mL), dried over sodium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with 3:1 isohexane:ethyl acetate. The fractions containing product were combined and evaporated to give the subtitled compound as a clear oil. Yield 1.23 g.
Workup
- stirringthe mixture stirred for 3 days
- stirringthe mixture stirred for 10 min
- customThe layers were separated
- extractionthe aqueous phase extracted with DCM (2×40 mL)
- washThe combined organic solutions were washed with brine (40 mL)
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customevaporated
- customPurification
- washeluting with 3:1 isohexane
- additionThe fractions containing product
- customevaporated
Sources & evidence
- ORD record
- ord-57b376b5797a4bc4bc60c372bbc6a37d
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629271B2
Reaction notes
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