Dimethylformamide → 1-Cyano-8-hydroxynaphthalene-3,6-disulfonic acid

HRID 269375

反応式

HRID 269375 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:9][C:10]=2[OH:12])[CH:5]=[C:4]([S:17]([OH:20])(=[O:19])=[O:18])[CH:3]=1.[CH3:21][N:22](C)C=O>O.[Cu+].[Cu]>[C:21]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:9][C:10]=2[OH:12])[CH:5]=[C:4]([S:17]([OH:20])(=[O:19])=[O:18])[CH:3]=1)#[N:22]

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 855198901-Bromo-8-hydroxynaphthalene-3,6-disulfonic acid

生成物 1

HCID 860575081-Cyano-8-hydroxynaphthalene-3,6-disulfonic acid収率 67%

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 104815Copper(1+)触媒HCID 962Water溶媒

実験手順

1-Bromo-8-hydroxynaphthalene-3,6-disulfonic acid (51% strength, 15.0 g, 0.02 mol, prepared as in Example 31, stage 1) was stirred in N,N-dimethylformamide (100 mls). Copper (I) cyamide (2.0 g, 0.022 mol) was added and the mixture boiled under reflux until HPLC analysis indicated complete reaction. In this example 5 hours was required. If necessary further copper cyamide could be added during the reaction. The reaction mixture was cooled down and a small amount of insoluble material removed by filtration. The solvent was removed from the filtrate under vacuum to leave a brown tar. This was slurried in water and a small amount of solid removed by filtration. The filtrate was concentrated to 100 mls and the product precipitated by the addition of solid sodium chloride. The product was recovered by filtration, washed with brine and dried. The dried product (8.9 g) contained 50% sodium chloride. Yield 67%.

後処理

  1. temperatureunder reflux until HPLC analysis
  2. customreaction
  3. customIn this example 5 hours
  4. temperatureThe reaction mixture was cooled down
  5. customa small amount of insoluble material removed by filtration
  6. customThe solvent was removed from the filtrate under vacuum
  7. customto leave a brown tar
  8. customa small amount of solid removed by filtration
  9. concentrationThe filtrate was concentrated to 100 mls
  10. customthe product precipitated by the addition of solid sodium chloride
  11. filtrationThe product was recovered by filtration
  12. washwashed with brine
  13. customdried

出典と根拠

ORDレコード
ord-252c967f1f5b4f9280dd0def84541b48
出典データセット
uspto-grants-2008_11
特許番号
US07446184B2

関連ノート

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