Ammonium Carbonate → HCID 67001458, compound

HRID 559510Notes

Reaction equation

HRID 559510 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:19][O:20][CH3:21])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=O)C.[O-:22][C:23]#[N:24].[K+].[C:26](=[O:29])([O-])[O-].[NH4+:30].[NH4+]>C(O)C.O>[O:22]=[C:23]1[NH:30][CH:1]([C:4]2[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:19][O:20][CH3:21])[C:14]3[S:15][CH:16]=[CH:17][N:18]=3)(=[O:12])=[O:11])=[CH:6][CH:5]=2)[C:26](=[O:29])[NH:24]1

Participants

6

Reactant 3

HCID 517111Ammonium CarbonateHCID 11378442Potassium cyanateHCID 67001470HCID 67001470, compound

Product 1

HCID 67001458HCID 67001458, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4-acetyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (0.45 mmol), potassium cyanate (1.53 mmol), and ammonium carbonate (4.5 mmol) in ethanol and water (5 mL, 1:1) was stirred at 135° C. in a microwave reactor for 10 min. The reaction mixture was quenched with 6N HCl aqueous solution. After neutralized with saturated NaHCO3, the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by reverse phase HPLC to give 4-(2,5-dioxo-imidazolidin-4-yl)-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (0.2 mmol).

Workup

  1. customThe reaction mixture was quenched with 6N HCl aqueous solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-117023a8d16042808095b086b9337c4f
Source dataset
uspto-grants-2011_11
Patent number
US08063080B2

Reaction notes

Loading…