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Dimethylformamide → 1-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine

HRID 1752595
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인쇄 미리보기

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HRID 1752595 반응식
O=S(Cl)[Cl:3].CN(C=O)C.[CH3:10][O:11][C:12]1[CH:32]=[CH:31][C:15]([CH2:16][N:17]2[CH:22]=[C:21]([CH2:23]O)[C:20]([C:25]([O:27][CH3:28])=[O:26])=[C:19]([Cl:29])[C:18]2=[O:30])=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[CH3:10][O:11][C:12]1[CH:32]=[CH:31][C:15]([CH2:16][N:17]2[CH:22]=[C:21]([CH2:23][Cl:3])[C:20]([C:25]([O:27][CH3:28])=[O:26])=[C:19]([Cl:29])[C:18]2=[O:30])=[CH:14][CH:13]=1
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참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 904219461-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-hydroxymethyl-pyridine

생성물 1

HCID 904218061-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine수율 29%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
70 °C

실험 절차

SOCl2 (0.1 ml, 1.370 mmol) and DMF (0.1 ml, 1.291 mmol) were each slowly added in sequence to a suspension of compound (11) (360 mg, 1.066 mmol) in CHCl3 (10 ml) and the reaction was stirred at 70° C. for about 3 h. The solvent was removed and the resulting mixture was deposited onto silica gel, loaded onto a silica gel column and eluted with MeOH/DCM (1:100) to afford the title compound (110 mg, 0.309 mmol, 29.0% yield). 1H-NMR (CDCl3, 400 MHz): δ=3.80 (s, 3H), 3.98 (s, 3H), 4.37 (s, 2H), 5.09 (s, 2H), 6.89 (d, 2H, J=8.0 Hz), 7.28 (d, 2H, J=8.0 Hz).

후처리

  1. customThe solvent was removed
  2. washeluted with MeOH/DCM (1:100)

출처 및 근거

ORD 기록
ord-516cba0ebee34b7ab53d372ce49d0fa8
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09163019B2

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