Hydrochloric Acid → Methyl 2-(methylthio)-4-ureidothiazole-5-carboxylate

HRID 1692796Notes

Reaction equation

HRID 1692796 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([S:10][CH3:11])=[N:7][C:6]=1[NH2:12])=[O:4].ClS([N:17]=[C:18]=[O:19])(=O)=O.Cl.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:11][S:10][C:8]1[S:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([NH:12][C:18]([NH2:17])=[O:19])[N:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 609212Methyl 4-amino-2-(methylsulfanyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 57685416Methyl 2-(methylthio)-4-ureidothiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

In 150 mL methylene chloride, 4-amino-2-methylthio-5-thiazolcarboxylic acid methyl ester (0.05 mol) was dissolved and cooled to −78° C. under nitrogen gas. Stirring, 0.07 mol (1.4 eq) of chlorosulfonyl isocyanate was added slowly to give a brown solution. The reaction was warmed slowly to 0° C. and a white precipitate forms. After 30 minutes, the solution was evaporated under vacuum, resuspended in 40 mL of 6N hydrochloric acid (4 eq) and heated to 100° C. After 30 minutes, the solution was cooled to room temp, neutralized with saturated sodium carbonate followed by saturated sodium bicarbonate. The white solid was isolated by filtration to give methyl 2-(methylthio)-4-ureidothiazole-5-carboxylate 76.

Workup

  1. customto give a brown solution
  2. temperatureThe reaction was warmed slowly to 0° C.
  3. customthe solution was evaporated under vacuum
  4. temperatureheated to 100° C
  5. waitAfter 30 minutes
  6. temperaturethe solution was cooled to room temp
  7. customThe white solid was isolated by filtration

Sources & evidence

ORD record
ord-929f052087f64083bef5fa97bb2e1509
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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