Ethyl bromoacetate → ethyl (2,4-dioxo-2H-3,1-benzoxazin-1(4H)-yl)acetate

HRID 539856Notes

Reaction equation

HRID 539856 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C)C=O>[O:12]=[C:5]1[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=2[C:2](=[O:3])[O:4]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8359Isatoic AnhydrideHCID 24758Sodium hydride

Product 1

HCID 3568603ethyl (2,4-dioxo-2H-3,1-benzoxazin-1(4H)-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Isatoic anhydride (10 g, 1 equiv) in dimethylformamide (30 ml) was added dropwise to a suspension of sodium hydride (2.45 g, 60% in mineral oil, 1 equiv) in dimethylformamide (70 ml) at room temperature. The reaction was stirred for 1 hour prior to the addition of ethyl bromoacetate (6.8 ml, 1 equiv) and the resulting mixture stirred for 16 hours. Solvent evaporated, the residue suspended in water and the solid collected. The title compound was obtained by crystallisation from ethyl acetate (10.5 g). 1H-NMR (CDCl3) δ 1.29 (3H, t), 4.27 (2H, q), 4.82 (2H, s), 6.96 (1H, d), 7.33 (1H, t), 7.74 (1H, dt), 8.19 (1H, dd).

Workup

  1. stirringthe resulting mixture stirred for 16 hours
  2. customSolvent evaporated
  3. customthe solid collected

Sources & evidence

ORD record
ord-72bcf90349b34f89ba636c3cc8d37c11
Source dataset
uspto-grants-2014_10
Patent number
US08871775B2

Reaction notes

Loading…