Iodine chloride → HCID 18980002, compound

HRID 2396470Notes

Reaction equation

HRID 2396470 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH:10]=[C:9]([O:13][CH3:14])[C:8](=[O:15])[NH:7][C:6]=2[CH:16]=1.C([O-])(=O)C.[Na+].[I:22]Cl>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([I:22])=[C:9]([O:13][CH3:14])[C:8](=[O:15])[NH:7][C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 150296358-Chloro-3-methoxy-1H-1-benzazepine-2,5-dione

Product 1

HCID 18980002HCID 18980002, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 8-chloro-3-methoxy-2,5-dioxo-2,5-dihydro-1H-benz[b]azepine (3.00 g) in glacial acetic acid (250 mL) was added sodium acetate (2.07 g) followed by iodine monochloride (15.2 mL). The mixture was heated to reflux for 1.5 hours, was allowed to cool, and the acetic acid was evaporated from the reaction mixture. The solid residue was suspended in tetrahydrofuran and stirred for 15 minutes. The solution was filtered and the resulting liltrate evaporated. The yellowish solid was recrystallized from refluxing toluene (700 mL) to afford the title compound (3.8 g); 250 MHz NMR: 11.60 (broad s, 1), 7.59 (d,1, J=7.1), 7.30 (d,1, J=1.4), 7.23 (dd,1, J=7.1, 1.6), 3.90 (s,3). Analysis for C11H7ClINO3 : Calculated: C, 36.34; H, 1.94; N, 3.85; Found: C, 36.35, H, 1.87; N, 3.82.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. customthe acetic acid was evaporated from the reaction mixture
  5. filtrationThe solution was filtered
  6. customThe yellowish solid was recrystallized
  7. temperaturefrom refluxing toluene (700 mL)

Sources & evidence

ORD record
ord-33ffc014453f40c29f2a84e639abf977
Source dataset
uspto-grants-1996_02
Patent number
US05492905

Reaction notes

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