2-Chloro-N,N-dimethylethylamine → 3-(Acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

HRID 1649327노트

반응식

HRID 1649327 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[NH:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:27][N:28]([CH2:30][CH2:31]Cl)[CH3:29].C(OC(C)C)(C)C>CCOCC.C(O)(=O)C.CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH:15]([O:16][C:17](=[O:19])[CH3:18])[C:14](=[O:20])[N:13]([CH2:31][CH2:30][N:28]([CH3:29])[CH3:27])[C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]=3[S:10]2)=[CH:7][CH:8]=1

참가 물질

8

반응물 4

HCID 79012-Chloro-N,N-dimethylethylamineHCID 7914Diisopropyl EtherHCID 24758Sodium hydrideHCID 591255Benzo[b][1,4]thiazepin-4(5H)-one, 2,3-dihydro-3-acetoxy-2-(4-methoxyphenyl)-2회

생성물 1

HCID 30763-(Acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one수율 76.2%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매

실험 절차

5-(1). 2-(4'-Methoxyphenyl)-3-acetoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one [Compound (II)] (1.0 g) and dried silica gel suitable for column chromatography (which is obtained by calcining a commercially available silica gel (Wako gel C-200) at 300° C. under nitrogen for 8 hours) (0.5 g) are added to dimethylsulfoxide (10 ml), and thereto is added a 60% by weight sodium hydride (0.14 g), and the mixture is stirred at room temperature for 30 minutes. A 50% by weight solution (0.75 g) of N,N-dimethylaminoethyl chloride in ether is added to the mixture, and the mixture is further stirred at room temperature for 5 hours and neutralized with acetic acid, and then, silica gel is filtered off. To the filtrate is added benzene, and the benzene solution is washed with water, dried, and evaporated to remove benzene to give a solid substance (1.20 g). The solid substance is added to diisopropyl ether. After removing the insoluble materials by filtration, the filtrate is allowed to stand at room temperature. The precipitated crystals are separated by filtration to give the title compound (I) (0.92 g, 76.2%), m.p. 134°-135° C. The hydrochloride of this product: m.p. 187°-188° C.

후처리

  1. customat 300° C.
  2. customfor 8 hours
  3. stirringthe mixture is further stirred at room temperature for 5 hours
  4. filtrationsilica gel is filtered off
  5. additionTo the filtrate is added benzene
  6. washthe benzene solution is washed with water
  7. customdried
  8. customevaporated
  9. customto remove benzene
  10. customto give a solid substance (1.20 g)
  11. customAfter removing the insoluble materials
  12. filtrationby filtration
  13. customto stand at room temperature
  14. customThe precipitated crystals are separated by filtration

출처 및 근거

ORD 기록
ord-eeda6be577fb445ab2a11dcf28ecfe20
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04416819

반응 노트

불러오는 중…