5-Fluoro-2-(4'-amino-3'-iodophenyl)benzothiazole → 2-Amino-5-(5-fluorobenzo[d]thiazol-2-yl)benzonitrile

HRID 25268Notes

Reaction equation

HRID 25268 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[C:12](I)[CH:11]=3)=[N:7][C:6]=2[CH:18]=1.[Cu](C#N)[C:20]#[N:21]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([C:20]#[N:21])[CH:11]=3)=[N:7][C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 3992495-Fluoro-2-(4'-amino-3'-iodophenyl)benzothiazoleHCID 178418260HCID 178418260, compound

Product 1

HCID 4028622-Amino-5-(5-fluorobenzo[d]thiazol-2-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Fluoro-2-(4′-amino-3′-iodophenyl)benzothiazole (5 g, 0.0135 mol), copper cyanide (3.65 g, 0.04 mol) and DMF (100 ml) were heated under reflux for 6 hrs, cooled and the solvent removed under vacuum. The residue was stirred in water (50 ml) for 30 mins, then the product extracted with ethyl acetate (2×100 ml). The combined extracts were dried (Na2SO4), evaporated and the residue recrystallised from ethanol to give a white solid.

Workup

  1. temperatureunder reflux for 6 hrs
  2. temperaturecooled
  3. customthe solvent removed under vacuum
  4. extractionthe product extracted with ethyl acetate (2×100 ml)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customevaporated
  7. customthe residue recrystallised from ethanol
  8. customto give a white solid

Sources & evidence

ORD record
ord-9446fc975140435fb7311e73e5cbd347
Source dataset
uspto-grants-2005_02
Patent number
US06858633B1

Reaction notes

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