Iodine → HCID 11845284, compound

HRID 915623Notes

Reaction equation

HRID 915623 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1.[N:15]([O-:17])=[O:16].[Na+].II.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:11]2[O:10][CH2:9][C:8]([N+:15]([O-:17])=[O:16])=[CH:7][C:6]=2[C:5]([C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 656671Sodium PyrosulfiteHCID 10878008HCID 10878008, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11845284HCID 11845284, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Into a reactor, equipped with a mechanic stirrer and a reflux condenser, 8-fluoro-2H-chromene-5-carboxylic acid amide (3.1 g; 15 mmoles), sodium nitrite (3.1 g; 45 mmoles) and toluene (30 ml) were charged at room temperature and under inert gas. The mixture was heated under stirring at 50° C., then iodine (1.9 g; 7.5 mmoles) and, slowly in 4 hours, Oxistrong 15® (3.7 ml) were added. At the end of the addition the reaction mixture was kept under stirring for a further hour, then cooled to 0° C. A 20% solution of sodium metabisulphite (about 15 ml) was added and the mixture was kept under stirring for 1 hour. After filtration the solid was washed with water (2×10 ml) and with toluene (10 ml) and dried in oven under vacuum at 50° C. overnight obtaining 8-fluoro-3-nitro-2H-chromene-5-carboxylic acid amide (3.4 g; titre 78%; 74% yield).

Workup

  1. customInto a reactor, equipped with a mechanic stirrer and a reflux condenser
  2. temperatureThe mixture was heated
  3. additionOxistrong 15® (3.7 ml) were added
  4. additionAt the end of the addition the reaction mixture
  5. stirringunder stirring for a further hour
  6. temperaturecooled to 0° C
  7. stirringunder stirring for 1 hour
  8. filtrationAfter filtration the solid
  9. washwas washed with water (2×10 ml) and with toluene (10 ml)
  10. customdried in oven under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-07240833fb11448cbb80392799edcf9d
Source dataset
uspto-grants-2007_09
Patent number
US07265251B2

Reaction notes

Loading…