Benzyl Bromide → HCID 86614821、化合物

HRID 1686159ノート

反応式

HRID 1686159 の反応式
[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

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 31347SulfolaneHCID 517045Sodium AcetateHCID 86614812HCID 86614812、化合物

生成物 1

HCID 86614821HCID 86614821、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0136782d0ba240c28014d32da03524f5
出典データセット
uspto-grants-2012_04
特許番号
US08148539B2

反応ノート

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