Water → HCID 68779576, compound

HRID 2262933Notes

Reaction equation

HRID 2262933 reaction equation
[NH2:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19].O>O1CCCC1>[Cl:23][C:22]([Cl:25])([Cl:24])[CH2:21][O:20][C:18]([NH:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 5072225Methyl 5-aminofuran-2-carboxylate

Product 1

HCID 68779576HCID 68779576, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-amino-2-furancarboxylate (1.00 g, 7.09 mmol) and pyridine (1.72 ml, 21.3 mmol) in tetrahydrofuran (24 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.96 ml, 14.2 mmol), and the mixture was stirred at room temperature for 1 hour and half. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 662 mg (29.6%) of the desired product as a solid was separated by filtration.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionHexane was poured to the residue, and 662 mg (29.6%) of the desired product as a solid
  7. customwas separated by filtration

Sources & evidence

ORD record
ord-99a0126e5e0b4eb39d34e91d553cc341
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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