Chlorosulfonyl isocyanate → Ethyl 3-ureidofuran-2-carboxylate

HRID 2098608Notes

Reaction equation

HRID 2098608 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].ClS([N:15]=[C:16]=[O:17])(=O)=O.[C:18]([O-])(O)=O.[Na+]>ClCCl>[NH:1]([C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([O:9][CH2:10][CH3:18])=[O:8])[C:16]([NH2:15])=[O:17]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 45790120Methyl 3-aminofuran-2-carboxylate

Product 1

HCID 59593138Ethyl 3-ureidofuran-2-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-aminofuran-2-carboxylate 34 (100 mg, 1.0 eq) in dichloromethane (3 ml) at −78° C. was added chlorosulfonyl isocyanate (0.09 ml, 1.4 eq) dropwise. The reaction was slowly warmed to room temperature and stirred for 40 minutes. Reaction was concentrated. To the residue was added 6N HCl (3.5 ml) and mixture was heated to 100° C. for 20 minutes. Reaction mixture was allowed to cool down to room temperature, and was neutralized with saturated aq. NaHCO3. Solid was collected by filtration to yield ethyl 3-ureidofuran-2-carboxylate 35 (120 mg, 92%) as a beige solid which was used in the next reaction without further purification.

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. additionTo the residue was added 6N HCl (3.5 ml) and mixture
  4. temperaturewas heated to 100° C. for 20 minutes
  5. customReaction mixture
  6. temperatureto cool down to room temperature
  7. filtrationSolid was collected by filtration

Sources & evidence

ORD record
ord-2e7e24c32ce941fbb24aec7c5fa97181
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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