Sodium Iodide → 6-Bromo-4-(methoxymethyl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1847027Notes

Reaction equation

HRID 1847027 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.C(N(CC)C(C)C)(C)C.[I-].[Na+].Cl[CH2:25][O:26][CH3:27]>ClCCCl.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:25][O:26][CH3:27])[C:6]=2[CH:12]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 867249556-Bromo-4-(methoxymethyl)-2H-1,4-benzoxazin-3(4H)-oneYield 88%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 6-bromo-2H-1,4-benzoxazin-3(4H)-one (13 g, 57 mmol) in 1,2-dichloroethane (350 ml) was cooled in an ice bath to which N,N-diisopropylethylamine (119 ml), sodium iodide (10.25 g, 68.4 mmol) and chloromethylmethyl ether (43.3 ml, 570 mmol) were added, and the mixture was stirred at 70° C. for 3 hours. After cooling, the reaction mixture was diluted with dichloromethane, washed with cold water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to yield 13.6 g (88%) of the title compound in the form of a light brown solid.

Workup

  1. additionwere added
  2. temperatureAfter cooling
  3. washwashed with cold water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-536cd7c559874531b9d1ef51e2660ee4
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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