Benzyl Bromide → HCID 86614821, 화합물

HRID 1686159노트

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HRID 1686159 반응식
[CH3:1][C:2]1[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([O-:18])(=[O:17])=[O:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:20]([O-:23])(=[O:22])=[O:21])[CH:8]=2)[N:3]=1.[Na+].[Na+].C([O-])(=O)C.[Na+].S1(CCCC1)(=O)=O.[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(OCC)(=O)C.CO>[CH2:38]([N+:3]1[C:4]2[C:9](=[CH:8][C:7]([S:20]([O-:23])(=[O:21])=[O:22])=[CH:6][CH:5]=2)[C:10]([CH3:19])([CH2:11][CH2:12][CH2:13][CH2:14][S:15]([OH:18])(=[O:16])=[O:17])[C:2]=1[CH3:1])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 31347SulfolaneHCID 517045Sodium AcetateHCID 86614812HCID 86614812, 화합물

생성물 1

HCID 86614821HCID 86614821, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

Disodium 2,3-dimethyl-3-(4-sulphonatobutyl)-3H-indole-5-sulphonate (5 g, 13.9 mmol) and sodium acetate (3.11 g) were stirred with methanol (100 ml) for 1 hour. Solvent removed by rotary evaporation and a further portion of methanol (100 ml) added. This was removed by rotary evaporation to yield an orange sticky solid. To this was added sulfolan (25 ml) and benzyl bromide (9.51 g, 55.6 mmol, 4 eq). The mixture was stirred overnight at 110° C. under a blanket of nitrogen. The cooled red solution was poured into stirring ethyl acetate (1 l) and the precipitate filtered off. The precipitate was washed with copious ethyl acetate and diethyl ether and then dried under vacuum. A sample was dissolved in water and analysed by reverse Phase TLC using acetonitrile modified with 0.1% TFA:water modified with 0.1% TFA (30:70). Separation yielded the product (Rf 0.6) and starting material (Rf 0.95). The product spot turned red on standing indicating quaternisation had taken place. Yield: 8 g.

후처리

  1. customSolvent removed by rotary evaporation
  2. additiona further portion of methanol (100 ml) added
  3. customThis was removed by rotary evaporation
  4. customto yield an orange sticky solid
  5. additionThe cooled red solution was poured
  6. filtrationthe precipitate filtered off
  7. washThe precipitate was washed with copious ethyl acetate and diethyl ether
  8. customdried under vacuum
  9. dissolutionA sample was dissolved in water
  10. customSeparation
  11. customyielded the product (Rf 0.6)

출처 및 근거

ORD 기록
ord-0136782d0ba240c28014d32da03524f5
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148539B2

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