Chlorosulfonyl isocyanate → Ethyl 3-ureidofuran-2-carboxylate

HRID 1365127Notes

Reaction equation

HRID 1365127 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-add6129d74aa4317bf92fc7403e3acd8
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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