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Water → 4-(4-Benzylidenecyclohexylamino)-3-methoxy-2-methylpyridine

HRID 1007
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HRID 1007 반응식
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.O=[C:34]1[CH2:39][CH2:38][CH:37]([NH:40][C:41]2[CH:46]=[CH:45][N:44]=[C:43]([CH3:47])[C:42]=2[O:48][CH3:49])[CH2:36][CH2:35]1.O>COCCOC.CCCCCC.CS(C)=O>[CH:2](=[C:34]1[CH2:39][CH2:38][CH:37]([NH:40][C:41]2[CH:46]=[CH:45][N:44]=[C:43]([CH3:47])[C:42]=2[O:48][CH3:49])[CH2:36][CH2:35]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
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참가 물질

8

반응물 4

HCID 962WaterHCID 2734970Benzyltriphenylphosphonium bromideHCID 196939514-(4-Oxocyclohexylamino)-3-methoxy-2-methylpyridineHCID 178418339Butyllithium

생성물 1

HCID 196939574-(4-Benzylidenecyclohexylamino)-3-methoxy-2-methylpyridine

시약·촉매·용매 3

HCID 679
Dimethyl Sulfoxide
용매
HCID 8058Hexane용매
HCID 80711,2-Dimethoxyethane용매

실험 절차

7.8 g of benzyltriphenylphosphonium bromide in 50 ml of ethylene glycol dimethyl ether are deprotonated at 10° to 20° C. using 11 ml of 1.6 molar butyllithium solution in hexane. After 30 minutes 1.3 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine are added dropwise in 10 ml of DMSO. After 5 hours at 40° to 50° C. the mixture is poured into water and extracted with methylene chloride. The product is purified by column chromatography on silica gel (eluent: ethanol). 0.6=41%; m.p.: 120° C.

후처리

  1. customare deprotonated at 10° to 20° C.
  2. extractionextracted with methylene chloride
  3. customThe product is purified by column chromatography on silica gel (eluent: ethanol)

출처 및 근거

ORD 기록
ord-13d9fefea0ad416fb3ed3b3104651c13
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05723450

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