Hydrochloric Acid → HCID 86611699, compound

HRID 559511Notes

Reaction equation

HRID 559511 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([N:16](COC)[C:17]3[S:18][CH:19]=[CH:20][N:21]=3)(=[O:15])=[O:14])=[CH:9][CH:8]=2)[C:4](=[O:25])[NH:3]1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].Cl.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:26]([N:3]1[C:4](=[O:25])[CH:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3[S:18][CH:19]=[CH:20][N:21]=3)(=[O:14])=[O:15])=[CH:9][CH:8]=2)[NH:6][C:2]1=[O:1])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 67001458HCID 67001458, compound

Product 1

HCID 86611699HCID 86611699, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 4-(2,5-dioxo-imidazolidin-4-yl)-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (0.1 mmol), benzyl bromide (0.2 mmol), and potassium carbonate (0.1 mmol) in DMF (5 mL) was stirred at 65° C. for 4 h. The reaction mixture was acidified with 6N HCl aqueous solution and was stirred for 30 min before neutralized with saturated NaHCO3. The mixture was extracted with ethyl acetate and 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-(1-benzyl-2,5-dioxo-imidazolidin-4-yl)-N-thiazol-2-yl-benzenesulfonamide (0.04 mmol).

Workup

  1. stirringwas stirred for 30 min
  2. extractionThe mixture was extracted with ethyl acetate and organic phase
  3. washwas 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-e9afae1c1165458e8ac0fa94de1ed655
Source dataset
uspto-grants-2011_11
Patent number
US08063080B2

Reaction notes

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