Benzylamine → N-Benzyl-6-chloro-nicotinamide

HRID 379420

반응식

HRID 379420 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 857488N-Benzyl-6-chloro-nicotinamide수율 78.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f426e954fa924d95960c823dc02caea5
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297375B1

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