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

HRID 269375

반응식

HRID 269375 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23978Copper촉매HCID 104815Copper(1+)촉매HCID 962Water용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-252c967f1f5b4f9280dd0def84541b48
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446184B2

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