Iodine → HCID 11385310, compound

HRID 1351193Notes

Reaction equation

HRID 1351193 reaction equation
[CH2:1]([C:4]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[C:10]2[C:5]=1[C:6]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[N:7][CH:8]=[N:9]2)[CH:2]=[CH2:3].[I:25]I>ClCCl.C(Cl)(Cl)Cl>[I:25][CH2:3][CH:2]1[CH2:1][C:4]2[C:5]3[C:6](=[N:7][CH:8]=[N:9][C:10]=3[CH:11]=[C:12]([O:16][CH3:17])[C:13]=2[O:14][CH3:15])[N:18]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 807IodineHCID 11174663HCID 11174663, compound

Product 1

HCID 11385310HCID 11385310, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-allyl-6,7-dimethoxy-quinazolin-4-yl)-phenyl-amine (0.12 g, 0.37 mmol) (from Example 15, Step E, supra) in dichloromethane (20 mL) was added I2 (0.24 g, 1.87 mmol). The reaction mixture was stirred at room temperature for 3 hours. The mixture was diluted with chloroform (100 mL), and washed with a saturated aqueous Na2SO3 solution. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (1:2:0.05) as eluent to give the desired 5-iodomethyl-7,8-dimethoxy-4-phenyl-5,6-dihydro-4H-1,3,4-triaza-phenalene as a pale yellow solid. (Yield 0.11 g, 66%).

Workup

  1. washwashed with a saturated aqueous Na2SO3 solution
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-de55435508314d15ba5f3c4678385809
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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