Iodine → 3-Iodo-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one

HRID 1687633Notes

Reaction equation

HRID 1687633 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]2[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:3]1=2.C(Cl)Cl.CN(CCN(C)C)C.[Si]([I:33])(C)(C)C.II>>[I:33][CH:7]1[CH2:8][C:2]([CH3:17])([CH3:1])[C:3]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:4]=2[NH:5][C:6]1=[O:9]

Participants

6

Reactant 5

HCID 807IodineHCID 6344DichloromethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 85247Trimethylsilyl iodideHCID 578538535,5-Dimethyl-8-nitro-4,5-dihydro-1H-benzo[B]azepin-2(3H)-one

Product 1

HCID 672643563-Iodo-5,5-dimethyl-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one

Conditions

Temperature
0 °C

Procedure

5,5-Dimethyl-8-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (4.00 g, 0.0171 mol) in Methylene chloride (54 mL, 0.84 mol) was cooled to 0° C., treated with TMEDA (7.73 mL, 0.05 mol) then treated dropwise with TMSI (7.29 mL, 0.05 mol). The mixture was stirred at 0° C. for 60 min after which solid Iodine (6.50 g, 0.0256 mol) was added in one portion and the mixture stirred at 0° C. for 60 min. The reaction was quenched with 10% Na2S2O3. Title compound isolated as a beige solid. (5.43 g, 88%) LCMS 361 (M+H).

Workup

  1. additionwas added in one portion
  2. customThe reaction was quenched with 10% Na2S2O3

Sources & evidence

ORD record
ord-96826cc47f164fee8a4ddd19a11b2370
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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