Triethylamine → 4,5-Dibromo-N-methoxy-N-methylfuran-2-carboxamide

HRID 271512Notes

Reaction equation

HRID 271512 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](Cl)=[O:9])[O:5][C:6]=1[Br:7].Cl.[CH3:12][NH:13][O:14][CH3:15].C(N(CC)CC)C>ClCCl>[CH3:15][O:14][N:13]([CH3:12])[C:8]([C:4]1[O:5][C:6]([Br:7])=[C:2]([Br:1])[CH:3]=1)=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 148737404,5-Dibromofuran-2-carbonyl chloride

Product 1

HCID 446297544,5-Dibromo-N-methoxy-N-methylfuran-2-carboxamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Step 1 (0.1 mol) in dichloromethane (300 ml) was cooled to 0° C. and treated with N,O-dimethylhydroxylamine hydrochloride (11.7 g, 0.12 mol) followed by triethylamine (36 ml, 0.36 mol). The mixture was allowed to warm to room temperature and stirred for 30 minutes The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and water. After separation of the layers, the organic phase was washed sequentially with 2M hydrochloric acid, water and brine, dried and concentrated in vacuo. The product was purified by silica gel chromatography eluting with ethyl acetate/hexane (1:1) to give the title compound (30.1 g, 96%); 1H NMR (CDCl3) 7.12 (1H, s), 3.78 (3H, s), 3.31 (3H, s).

Workup

  1. customwas evaporated in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. customAfter separation of the layers
  4. washthe organic phase was washed sequentially with 2M hydrochloric acid, water and brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by silica gel chromatography
  8. washeluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-67d1eb100f8a414581bc453c77ca0370
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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