Sodium hydride → HCID 19737995, compound

HRID 2255509Notes

Reaction equation

HRID 2255509 reaction equation
[OH:1][CH:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[S:5](=[O:12])(=[O:11])[NH:4][CH2:3]1.[H-].[Na+].[N:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1>CN(C=O)C>[OH:1][CH:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[S:5](=[O:12])(=[O:11])[N:4]([CH2:21][C:18]2[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 745714-(Chloromethyl)pyridineHCID 229019424-Hydroxy-3,4-dihydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-1,1(2H)-dione

Product 1

HCID 19737995HCID 19737995, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

The product from Step C of Example 2 (4.0 g, 19.5 mmol) was dissolved in anhydrous DMF (20 mL) and cooled to -10° C. and sodium hydride (21.5 mmol) was added. After stirring for 40 min at room temperature, a solution of 4-picolyl chloride (3.7 g, 29.2 mmol) in DMF (15 mL) was added to the chilled (0° C.) reaction mixture. The mixture was allowed to warm to room temperature and stir for 18 h. The solution was concentrated and the residue was suspended in saturated sodium bicarbonate (50 mL) and the desired subject was collected by filtration. Recrystallization from ethanol gave a beige solid (4.9 g, 85%): mp 183°-185° C.

Workup

  1. temperaturechilled
  2. custom(0° C.) reaction mixture
  3. temperatureto warm to room temperature
  4. stirringstir for 18 h
  5. concentrationThe solution was concentrated
  6. filtrationwas collected by filtration
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-2945dc394f5647b29eb6be6d35980b3b
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

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