Dimethylformamide → HCID 67062707, compound

HRID 598879Notes

Reaction equation

HRID 598879 reaction equation
[Cl:1][C:2]1[S:6][N:5]=[C:4]([NH2:7])[N:3]=1.[O:8](C(OC(C)(C)C)=O)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O.CN(C=O)C.[H-].[Na+]>[NH4+].[Cl-].O.CCOC(C)=O>[Cl:1][C:2]1[S:6][N:5]=[C:4]([NH:7][C:9](=[O:8])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[N:3]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 90495Di-tert-butyl dicarbonateHCID 3192105-chloro-1,2,4-thiadiazol-3-amine

Product 1

HCID 67062707HCID 67062707, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred solution of 5-chloro-1,2,4-thiadiazol-3-amine (0.93 g, 6.9 mmol) and BOC2O (2.9 mL, 12 mmol) in DMF (10 mL, 129 mmol) was added sodium hydride (60%) (0.55 g, 14 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was carefully diluted with aqueous NH4Cl and water (20 mL each) and diluted with EtOAc (15 mL). The separated aqueous layer was extracted with EtOAc (15 mL×2) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a residue which was purified with flash column chromatography (ISCO Combiflash system, pure hexanes→10% EtOAc in hexanes) to obtain the desired product (0.87 g, 54%) as an off-white solid. LCMS (API-ES) m/z (%): 180.6 (100%, (M++H)-tert-Bu); 1H NMR (400 MHz, CD3OD) δ ppm (1.55, s, 9H).\

Workup

  1. extractionThe separated aqueous layer was extracted with EtOAc (15 mL×2)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas purified with flash column chromatography (ISCO Combiflash system, pure hexanes→10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e9c270cce2d34772a70a054cd2595733
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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