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Dichloromethane → 5-[3-chloro-5-(1-chloroethyl)-2-cyano-6-methoxyphenyl]-N,N-dimethylpyridine-2-carboxamide

HRID 1499898
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HRID 1499898 반응식
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([C:28]#[N:29])=[C:8]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[N:21][CH:22]=2)[C:9]([O:15][CH3:16])=[C:10]([CH:12](O)[CH3:13])[CH:11]=1.C(Cl)[Cl:31]>CN(C)C=O>[Cl:5][C:6]1[C:7]([C:28]#[N:29])=[C:8]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[N:21][CH:22]=2)[C:9]([O:15][CH3:16])=[C:10]([CH:12]([Cl:31])[CH3:13])[CH:11]=1
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참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 866778205-[3-chloro-2-cyano-5-(1-hydroxyethyl)-6-methoxyphenyl]N,N-dimethylpyridine-2-carboxamide

생성물 1

HCID 866778215-[3-chloro-5-(1-chloroethyl)-2-cyano-6-methoxyphenyl]-N,N-dimethylpyridine-2-carboxamide수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

Thionyl chloride (800 μL, 10 mmol) was added dropwise to a solution of 5-[3-chloro-2-cyano-5-(1-hydroxyethyl)-6-methoxyphenyl]N,N-dimethylpyridine-2-carboxamide (2 g, 6 mmol), methylene chloride (100 mL) and N,N-dimethylformamide (100 μL) at room temperature. The reaction was stirred for 5 hrs and was complete by LC/MS. The reaction mixture was partitioned between EtOAc and water. The combined organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4, filtered and concentrated to give crude 5-[3-chloro-5-(1-chloroethyl)-2-cyano-6-methoxyphenyl]-N,N-dimethylpyridine-2-carboxamide as an oil (1.8 g, 80%). LCMS calculated for C18H18Cl2N3O2(M+H)+: m/z=378.1; found: 378.1.

후처리

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washThe combined organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-246526a2d2c84aa3af3216f2268ff34e
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199982B2

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