Iodine → HCID 11845284, compound

HRID 1531433Notes

Reaction equation

HRID 1531433 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]([NH2:14])=[O:13])=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]=[CH:7]2.[N:15]([O-:17])=[O:16].[Na+].II>C(OCC)(=O)C.C(O)CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]([NH2:14])=[O:13])=[C:6]2[C:11]=1[O:10][CH2:9][C:8]([N+:15]([O-:17])=[O:16])=[CH:7]2

Participants

7

Reactant 3

HCID 807IodineHCID 10878008HCID 10878008, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11845284HCID 11845284, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolvent2×HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 8-fluoro-2H-1-benzopyran-5-carboxamide (4.46 g, 23.1 mmol) in ethyl acetate (220 mL), ethylene glycol (4.0 mL) and a solution of sodium nitrite (6.52 g, 92.4 mmol) in H2O (11 mL) were added followed by iodine (9.0 g, 34.7 mmol). The reaction mixture was refluxed for 24 hours and during this time H2O (22 mL) and ethylene glycol (4.0 mL) were added portionwise. The reaction mixture was cooled, diluted with ethyl acetate, washed with a 5% solution of NaS2O3, treated with brine, dried with MgSO4, filtered, and the solvent was removed in vacuo to give a crude yellow solid. The solid was recrystallized from absolute ethanol to give 1.3 g (24% yield) of sparkly yellow crystals as the title compound (mp 227.8-228.2° C.). EIMS (70 eV) m/z (relative intensity) 238 (57, M+), 221 (100), 192 (71), 191 (46), 190 (10), 148 (14), 109 (16), 94 (12).

Workup

  1. additionwere added portionwise
  2. temperatureThe reaction mixture was cooled
  3. washwashed with a 5% solution of NaS2O3
  4. additiontreated with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customto give a crude yellow solid
  9. customThe solid was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-24e78b4bbdf042179ffc431dfa389746
Source dataset
uspto-grants-2001_03
Patent number
US06197978B1

Reaction notes

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