Dimethylformamide → 4-(Cyanomethyl)benzoyl chloride
反応式
[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]参加物
実験手順
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.
後処理
- temperaturewas refluxed for three hours
- temperaturecooled
- concentrationconcentrated
- dissolutiondissolved in hot EtOAc
- additiontreated with activated charcoal
- filtrationfiltered through Celite
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-40435f3fb1c246db8964f0b3ad205001
- 出典データセット
- uspto-grants-1998_07
- 特許番号
- US05776983
反応ノート
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