Methyl iodide → HCID 54677724, compound

HRID 463667Notes

Reaction equation

HRID 463667 reaction equation
[OH:1][C:2]1[C:7]2[S:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:6]=2[S:5](=[O:16])(=[O:15])[NH:4][C:3]=1[C:17]([O:19][CH3:20])=[O:18].[H-].[Na+].[CH3:23]I>CN(C)C=O>[OH:1][C:2]1[C:7]2[S:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:6]=2[S:5](=[O:16])(=[O:15])[N:4]([CH3:23])[C:3]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54677723HCID 54677723, compound

Product 1

HCID 54677724HCID 54677724, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution, cooled to -2°, of 5.65 g of 4-hydroxy-3-methoxycarbonyl-6-trifluoromethyl-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide in 62 ml of absolute dimethylformamide is treated portionwise under a strong nitrogen stream with 0.87 g of sodium hydride (washed with benzene), the mixture is stirred at 5° for an additional 1.5 hours, then 1.49 ml of methyl iodide are added thereto in one portion, the temperature rising to about 15°. The mixture is stirred at room temperature for an additional 1.5 hours and then evaporated in vacuo. The residue is partitioned between 2N hydrochloric acid and methylene chloride, the aqueous phase is extracted three times with methylene chloride, the combined organic extracts are dried over sodium sulfate and evaporated. The brown crystalline residue is digested with about 50 ml of ethanol, the almost colorless crystals are removed by filtration under suction and washed with methanol. After recrystallization from ethanol, there is obtained 4-hydroxy-3-methoxycarbonyl-2-methyl-6-trifluoromethyl-2H-thieno[ 2,3-e]-1,2-thiazine 1,1-dioxide of melting point 178°-180°.

Workup

  1. customrising to about 15°
  2. stirringThe mixture is stirred at room temperature for an additional 1.5 hours
  3. customevaporated in vacuo
  4. customThe residue is partitioned between 2N hydrochloric acid and methylene chloride
  5. extractionthe aqueous phase is extracted three times with methylene chloride
  6. dry with materialthe combined organic extracts are dried over sodium sulfate
  7. customevaporated
  8. customthe almost colorless crystals are removed by filtration under suction
  9. washwashed with methanol
  10. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-bde13d303a4e487b9c2d24599362688f
Source dataset
uspto-grants-1985_10
Patent number
US04544655

Reaction notes

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