Chlorosulfonyl isocyanate → HCID 57685407, compound

HRID 1692755Notes

Reaction equation

HRID 1692755 reaction equation
[C:1]1([C:7]2[S:8][C:9]([NH2:17])=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClS([N:22]=[C:23]=[O:24])(=O)=O.C([O-])(O)=O.[Na+]>ClCCl>[C:1]1([C:7]2[S:8][C:9]([NH:17][C:23]([NH2:22])=[O:24])=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 13514498Ethyl 5-amino-2-phenyl-1,3-thiazole-4-carboxylate

Product 1

HCID 57685407HCID 57685407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-phenyl-5-aminothiazole-4-carboxylate (116 mg, 1.0 eq) in dichloromethane (3 ml) at −78° C. was added chlorosulfonyl isocyanate (0.06 ml, 1.3 eq) dropwise (Redman et al J. (2000) Org. Lett. 2:2061-2063). The reaction was slowly warmed to room temperature and stirred for 40 minutes. The reaction was concentrated. To the residue was added 6N HCl (2.5 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 2-phenyl-5-ureidothiazole-4-carboxylate 63 as a beige solid which was used in the next reaction without further purification.

Workup

  1. concentrationThe reaction was concentrated
  2. additionTo the residue was added 6N HCl (2.5 ml) and mixture
  3. temperaturewas heated to 100° C. for 20 minutes
  4. customReaction mixture
  5. temperatureto cool down to room temperature
  6. filtrationSolid was collected by filtration

Sources & evidence

ORD record
ord-f05e55d51e4d4900a22dd70008ad1de9
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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