Iodine → HCID 68452177, compound

HRID 1687698Notes

Reaction equation

[CH2:1]([N:3]1[C:9](=[O:10])[CH2:8][CH2:7][CH2:6][C:5]2[C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:4]1=2)[CH3:2].CN(C)CCN(C)C.[I:28][Si](C)(C)C.II>C(Cl)Cl>[CH2:1]([N:3]1[C:9](=[O:10])[CH:8]([I:28])[CH2:7][CH2:6][C:5]2[C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:4]1=2)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

1-Ethyl-6-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1.0 g) in Methylene chloride (12 mL) was cooled to 0° C. and treated with N,N,N′,N′-Tetramethylethylenediamine (1.7 mL) then treated dropwise with Iodotrimethylsilane (1.6 mL). A white precitate formed in the solution. The mixture was stirred at 0° C. for 30 min, solid Iodine (1.4 g) was added in one portion and the mixture stirred at 0° C. A dark color ensued. After 45 min, the reaction was quenched with 10% Na2S2O3, extracted with dichloromethane. The organic layers were washed with brine, dried (MgSO4), filtered and concentrated. (+/−)-1-Ethyl-3-iodo-6-methoxy-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one isolated as an orangish solid (1.30 g, 88%). LC/MS: (M+H)+ found 390.93. Taking on without purification.

Workup

customA white precitate formed in the solution
stirringthe mixture stirred at 0° C
waitAfter 45 min
customthe reaction was quenched with 10% Na2S2O3
extractionextracted with dichloromethane
washThe organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-637406d3109c49379efaa5c8033739ab
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

Loading…