Diethyl Ether → HCID 58476643, compound

HRID 1892178Notes

Reaction equation

HRID 1892178 reaction equation
[Cl:1][C:2]1[C:14]([I:15])=[CH:13][C:5]2[C:6](=[O:12])[CH2:7][CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.[CH3:16][N:17]([CH:19](OC)OC)[CH3:18].CCOCC>C1COCC1>[Cl:1][C:2]1[C:14]([I:15])=[CH:13][C:5]2[C:6](=[O:12])/[C:7](=[CH:16]\[N:17]([CH3:19])[CH3:18])/[CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 78373Dimethylformamide dimethyl acetalHCID 584765998-Chloro-3,4-dihydro-7-iodo-1H-1-benzazepine-2,5-dione

Product 1

HCID 58476643HCID 58476643, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 8-chloro-7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione (10.0 g, 29.8 mmol) in THF (44 mL) was added DMF-DMA (21.1 mL, 149 mmol). The flask reaction mixture was allowed to stir 60° C. under an atmosphere of argon. A light orange solution containing a suspended solid resulted. After 17 h, the reaction mixture was allowed to cool to rt. Ether (100 mL) was added and the solid was collected via suction filtration, washed with ether, and dried in a vacuum oven to yield (4Z)-8-chloro-4-[(dimethylamino)methylene]-7-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione (9.50 g, 24.3 mmol, 82%) as a yellow solid. LCMS (FA): m/z=391 (M+H).

Workup

  1. customThe flask reaction mixture
  2. additionA light orange solution containing a suspended solid
  3. customresulted
  4. temperatureto cool to rt
  5. filtrationthe solid was collected via suction filtration
  6. washwashed with ether
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-92014f1bc9984677b907b4893193dabd
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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