Sodium Iodide → HCID 68137895, compound

HRID 1287226Notes

Reaction equation

HRID 1287226 reaction equation
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]1.[H-].[Na+].[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17]Cl.[I-].[Na+].[CH3:22][N:23](C=O)[CH3:24]>C1(C)C=CC=CC=1>[CH3:14][N:15]([CH3:19])[CH:16]([N:23]([CH3:24])[CH3:22])[CH2:17][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[S:1][CH2:2][C:3]1=[O:11]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 79012-Chloro-N,N-dimethylethylamineHCID 213964H-1,4-Benzothiazin-3-oneHCID 24758Sodium hydride

Product 1

HCID 68137895HCID 68137895, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 108 g of 1,4-benzothiazin-3(4H)-one in 650 ml of DMF is stirred and treated portionwise with 32.5 g of sodium hydride (50% dispersion) while maintaining the temperature below 50°. The solution is then heated to 70°, cooled to 25° and treated with 350 ml of 2.8 N toluene solution of 2-dimethylaminoethyl chloride and 6 g of sodium iodide. This mixture is heated at 100°-105° for 3 hours, cooled, poured into 2 liters of ice-water, and extracted with 500 ml of ether (three times). The organic phases are combined and extracted with a solution of 120 ml of concentrated HCl in 500 ml of water. The aqueous phase is cooled and treated portionwise with 240 g of K2CO3. The liberated base is extracted with 500 ml of ether (three times), the organic phases are combined, dried (MgSO4), filtered and the solvent evaporated. The residue is fractionated to give 103.5 g of colorless product; b.p. 146°-149° (0.2 mm).

Workup

  1. temperaturewhile maintaining the temperature below 50°
  2. temperatureThe solution is then heated to 70°
  3. temperaturecooled to 25°
  4. temperatureThis mixture is heated at 100°-105° for 3 hours
  5. temperaturecooled
  6. extractionextracted with 500 ml of ether (three times)
  7. extractionextracted with a solution of 120 ml of concentrated HCl in 500 ml of water
  8. temperatureThe aqueous phase is cooled
  9. additiontreated portionwise with 240 g of K2CO3
  10. extractionThe liberated base is extracted with 500 ml of ether (three times)
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. customthe solvent evaporated

Sources & evidence

ORD record
ord-b7dea13ad7d342998113ba69b49a4a64
Source dataset
uspto-grants-1976_10
Patent number
US03984405

Reaction notes

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