Sodium Iodide → HCID 66987547, 화합물

HRID 555274노트

반응식

HRID 555274 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:12][CH2:13][OH:14])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4].[H-].[Na+].[CH3:19][S:20][CH2:21]Cl.[Na+].[I-]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].COCCOC.C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:12][CH2:13][O:14][CH2:19][S:20][CH3:21])[CH:10]=[N:11][C:7]=2[CH:6]=1)=[O:4]

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 66987301HCID 66987301, 화합물

생성물 1

HCID 66987547HCID 66987547, 화합물수율 83.3%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 8028Tetrahydrofuran용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 1-(2-hydroxyethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (0.5 g. 2.27 mmol) in a mixture of dry THF:DME (25 mL:15 mL) was cooled to 5° C. NaH (0.081 g, 3.4 mmol) was added and stirred for 30 min at the same temperature. A mixture of chloromethyl methyl sulphide (0.285 g, 2.95 mmol) and NaI (0.408 g, 2.95 mmol) was then added slowly followed by TBAI (0.087 g, 0.22 mmol). The reaction was allowed to stir for overnight at ambient temperature. It was then quenched with saturated ammonium chloride solution and extracted with EtOAc. The organic layer was evaporated to give 0.53 g (83%) of 1-(2-methylsulfanylmethoxyethyl)-1H-benzimidazole-5-carboxylic acid methyl ester. 1H NMR (300 MHz, CDCl3) δ 1.9 (s, 3H), 3.9 (t, 2H), 3.95 (s, 3H), 4.4 (t, 2H), 4.6 (s, 2H), 7.45 (d, 1H), 8.05 (m, 2H), 8.5 (d, 1H)

후처리

  1. additionwas then added slowly
  2. stirringto stir for overnight at ambient temperature
  3. customIt was then quenched with saturated ammonium chloride solution
  4. extractionextracted with EtOAc
  5. customThe organic layer was evaporated

출처 및 근거

ORD 기록
ord-c77c16136906438694f71f21c8229dd7
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053431B2

반응 노트

불러오는 중…