Dimethylformamide → HCID 19738008, compound

HRID 2255498Notes

Reaction equation

HRID 2255498 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])NC1.[H-].[Na+].[CH3:15]I.C[N:18]([CH:20]=O)[CH3:19]>>[CH3:15][O:1][CH:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[S:5](=[O:12])(=[O:11])[N:18]([CH3:19])[CH2:20]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 229019424-Hydroxy-3,4-dihydro-1lambda~6~-thieno[3,2-e][1,2]thiazine-1,1(2H)-dione

Product 1

HCID 19738008HCID 19738008, compound

Procedure

To a solution of the product from Step C. (2.75 g, 13.4 mmol) in anhydrous DMF (40 mL) cooled to 0° C. was added sodium hydride (60% dispersion in mineral oil, 1.18 g, 29.5 mmol), followed by methyl iodide (2.5 mL, 40.2 mmol). The reaction mixture stirred at ambient temperature for 4 h and was poured onto ice and extracted with ethyl acetate (3×80 mL). Evaporation gave 3.35 g of an orange liquid which was chromatographed (silica, eluting with 50% ethyl acetate-hexane) to give the desired product (2.42 g, 77%): mp 61°-63° C.

Workup

  1. additionwas poured onto ice
  2. extractionextracted with ethyl acetate (3×80 mL)
  3. customEvaporation

Sources & evidence

ORD record
ord-7f5363a1eae3481aa8573db1c8e55eee
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

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