Bromine → HCID 15615543, compound

HRID 1194321Notes

Reaction equation

HRID 1194321 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]([C:5]1[O:6][C:7]([C:10](=[O:12])[CH3:11])=[CH:8][CH:9]=1)=[O:4].[Br:14]Br>C(O)(=O)C>[CH3:13][N:2]([CH3:1])[C:3]([C:5]1[O:6][C:7]([C:10](=[O:12])[CH2:11][Br:14])=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 15615542HCID 15615542, compound

Product 1

HCID 15615543HCID 15615543, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.81 g. (0.01 mole) of N,N-dimethyl-5-acetylfuran-2-carboxamide, 1.59 g. (0.01 mole) of bromine and 40 ml. of glacial acetic acid was stirred at room temperature for 18 hours, and then the acetic acid was removed by evaporation in vacuo. The residue was partitioned between water and ethyl acetate and the layers were separated. The aqueous layer was further extracted with ethyl acetate, and the combined ethyl acetate solutions were washed with sodium bicarbonate solution followed by water, dried (Na2SO4) and evaporated in vacuo. This afforded 2.6 g. of the title compound as a solid.

Workup

  1. additionA mixture of 1.81 g
  2. customthe acetic acid was removed by evaporation in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. customthe layers were separated
  5. extractionThe aqueous layer was further extracted with ethyl acetate
  6. washthe combined ethyl acetate solutions were washed with sodium bicarbonate solution
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-944df5bfcab44d2294ab2d8884307d1c
Source dataset
uspto-grants-1989_03
Patent number
US04814341

Reaction notes

Loading…