Acetonitrile → 1,1'-(Disulphanediyldiethane-2,1-diyl)bis(4-methylpyridinium)dibromide

HRID 420414

반응식

HRID 420414 반응식
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[Br:8][CH2:9][CH2:10][S:11][S:12][CH2:13][CH2:14]Br.[CH3:16][N:17]1[CH2:21][CH2:20][CH2:19][C:18]1=O.[C:23](#N)C>>[Br-:8].[Br-:8].[S:12]([CH2:13][CH2:14][N+:17]1[CH:16]=[CH:23][C:19]([CH3:18])=[CH:20][CH:21]=1)[S:11][CH2:10][CH2:9][N+:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1

참가 물질

5

반응물 4

HCID 6342AcetonitrileHCID 79634-MethylpyridineHCID 13387N-methyl-2-pyrrolidoneHCID 572268Disulfide, bis(2-bromoethyl)

생성물 1

HCID 866303221,1'-(Disulphanediyldiethane-2,1-diyl)bis(4-methylpyridinium)dibromide수율 90%

반응 조건

온도
85 °C

실험 절차

67 g of 4-picoline were diluted in 100 ml of acetonitrile and the mixture was brought to 80° C. A mixture of 60 g of 1-bromo-2-[(2-bromoethyl)disulphanyl]ethane and 15 ml of N-methylpyrrolidone (NMP) was added over 5 min. After stirring for 4 h at 85° C., the mixture was cooled. The solid obtained was filtered, rinsed with 3×200 ml of acetonitrile then dissolved in 800 ml of isopropanol (under reflux). After cooling, 1 l of ethyl ether was added. The precipitate formed was filtered, rinsed with 3×200 ml of ethyl ether, then dried. The off-white powder obtained (73.77 g) very predominantly contained (>90%) the expected product which was used as such for the following step.

후처리

  1. customwas brought to 80° C
  2. additionwas added over 5 min
  3. temperaturethe mixture was cooled
  4. customThe solid obtained
  5. filtrationwas filtered
  6. washrinsed with 3×200 ml of acetonitrile
  7. dissolutionthen dissolved in 800 ml of isopropanol (under reflux)
  8. temperatureAfter cooling
  9. addition1 l of ethyl ether was added
  10. customThe precipitate formed
  11. filtrationwas filtered
  12. washrinsed with 3×200 ml of ethyl ether
  13. customdried
  14. customThe off-white powder obtained (73.77 g)

출처 및 근거

ORD 기록
ord-2721f4de1b234b248592a9f78d769c1a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097044B2

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