Dimethylformamide → 4-(Cyanomethyl)benzoyl chloride
Reaction equation
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)#[N:2].CN(C=O)C.S(Cl)([Cl:20])=O>>[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([Cl:20])=[O:9])=[CH:6][CH:5]=1)#[N:2]Participants
Procedure
A solution of 4-cyanomethylbenzoic acid (10.0 g, 62.2 mmol) in thionyl chloride (65 mL) containing DMF (1 mL) was refluxed for three hours, cooled, concentrated, dissolved in hot EtOAc, treated with activated charcoal, filtered through Celite, and concentrated to yield 4-cyanomethylbenzoyl chloride. 4-Cyanomethylbenzoyl chloride was converted to the title compound following the procedure described in step A of Example 82 with the following modifications: 1) 1-(4-cyanomethylphenyl)-2-phenylethanone was chromatographed on silica gel using 2:3 EtOAc/hexane; 2) purification of N-[1-(4-cyanomethylphenyl)-2-phenylethyl]formamide entailed treatment with activated charcoal in EtOAc followed by recrystallization from EtOAc/hexane; and 3) the title compound was chromatographed on silica gel eluting with 10% acetone/EtOAc.
Workup
- temperaturewas refluxed for three hours
- temperaturecooled
- concentrationconcentrated
- dissolutiondissolved in hot EtOAc
- additiontreated with activated charcoal
- filtrationfiltered through Celite
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-40435f3fb1c246db8964f0b3ad205001
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05776983
Reaction notes
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