Sodium Bicarbonate → HCID 18510995, compound

HRID 1370276Notes

Reaction equation

HRID 1370276 reaction equation
Cl.[CH3:2][C:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]([NH:23][C:24](=[O:27])[CH2:25]Cl)[S:15][C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=1)([CH3:5])[CH3:4].[O-][C:29]#[N:30].[Na+].C(=O)([O-])O.[Na+]>CS(C)=O>[NH2:30][C:29]1[N:13]2[C:12]([C:9]3[CH:10]=[CH:11][C:6]([C:3]([CH3:5])([CH3:4])[CH3:2])=[CH:7][CH:8]=3)=[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[S:15][C:14]2=[N:23][C:24](=[O:27])[CH:25]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 18510991HCID 18510991, compound

Product 1

HCID 18510995HCID 18510995, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-[4-[4-(1,1-dimethylethyl)phenyl]-5-(4-pyridyl)-1,3-thiazol-2-yl]-2-chloroacetamide hydrochloride (1.0 g) in dimethylsulfoxide (5 mL) was added sodium cyanate (0.24 g). The mixture was stirred at room temperature for 14 hours. An aqueous solution of sodium hydrogen carbonate was added to the reaction mixture and the mixture was extracted with a mixed solvent of ethyl acetate-tetrahydrofuran (1:1). The extract was washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was concentrated under reduced pressure and the residue was purified with silica gel column chromatography (hexane-tetrahydrofuran, 1:1) and recrystallized from ethyl acetate to obtain the title compound (0.14 g, yield 24%).

Workup

  1. extractionthe mixture was extracted with a mixed solvent of ethyl acetate-tetrahydrofuran (1:1)
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe residue was purified with silica gel column chromatography (hexane-tetrahydrofuran, 1:1)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-abece615681542518083e032db12e54d
Source dataset
uspto-grants-2003_06
Patent number
US06583146B1

Reaction notes

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