Benzylamine → N-Benzyl-6-chloro-nicotinamide

HRID 379420

反応式

HRID 379420 の反応式
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][N:7]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:15]([NH:22][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:6]([Cl:5])=[N:7][CH:8]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 7504BenzylamineHCID 24386Thionyl ChlorideHCID 792226-Chloronicotinic acidHCID 516892Sodium Bicarbonate

生成物 1

HCID 857488N-Benzyl-6-chloro-nicotinamide収率 78.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

3.5 ml (47.6 mMol) Thionylchloride and 50 μl DMF were added to a suspension of 5.0 g (31.7 mMol) 6-chloronicotinic acid in 50 ml toluene and the reaction mixture was heated at 80° C. for 2 hours. The solvent and excess thionyl chloride were removed under reduced pressure and the residue was dissolved in 50 ml dichloromethane. After cooling to 0° C., 10.4 ml (95.2 mMol) benzylamine were added over 20 minutes and after 30 minutes further stirring at room temperature, the reaction mixture was poured onto 50 ml aqueous saturated sodium bicarbonate solution. Extraction with dichloromethane, followed by crystallization from ethyl acetate/n-hexane 2:1 gave 6.13 g (78%) N-benzyl-6-chloro-nicotinamide as light brown crystals of m.p.=113-114° C.

後処理

  1. customThe solvent and excess thionyl chloride were removed under reduced pressure
  2. dissolutionthe residue was dissolved in 50 ml dichloromethane
  3. temperatureAfter cooling to 0° C.
  4. extractionExtraction with dichloromethane
  5. customfollowed by crystallization from ethyl acetate/n-hexane 2:1

出典と根拠

ORDレコード
ord-f426e954fa924d95960c823dc02caea5
出典データセット
uspto-grants-2001_10
特許番号
US06297375B1

関連ノート

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