Sodium Carbonate → HCID 15516318, compound

HRID 2371050Notes

Reaction equation

HRID 2371050 reaction equation
CS(O[CH2:6][CH:7]1[C:12]2[N:13]=[C:14]([NH2:16])[S:15][C:11]=2[CH2:10][CH2:9][CH2:8]1)(=O)=O.[N-:17]=[N+]=[N-].[Na+].C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.O>[NH2:17][CH2:6][CH:7]1[C:12]2[N:13]=[C:14]([NH2:16])[S:15][C:11]=2[CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 86682374HCID 86682374, compound

Product 1

HCID 15516318HCID 15516318, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-4-yl)methyl methanesulfonate (3.3 mmol) in DMF (10 mL) was added NaN3 (0.21 g, 3.3 mmol). The resulting mixture was stirred at 85° C. for 30 minutes. The mixture was poured into water (100 mL) and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was dissolved in THF (20 mL) and H2O (10 mL), Na2CO3 (0.35 g, 3.3 mmol) and PPh3 (0.8 g, 3 mmol) was added. After stirring overnight, the reaction mixture was diluted with water (100 mL) and then filtered. The filtrate was extracted with EtOAc, and the organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was obtained and used directly in the next step without further purification.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationAfter filtration and concentration
  5. dissolutionthe crude product was dissolved in THF (20 mL)
  6. stirringAfter stirring overnight
  7. filtrationfiltered
  8. extractionThe filtrate was extracted with EtOAc
  9. washthe organic layer was washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-8d17e121193242baa788dd2e08e21c19
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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