Sodium hydride → HCID 20492743, compound

HRID 434494Notes

Reaction equation

HRID 434494 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:17]=[CH:16][C:7]2[N:8]([CH3:15])[C:9](=[O:14])[CH2:10][S:11](=[O:13])(=[O:12])[C:6]=2[CH:5]=1.[Na].C([C:21]([O:23][CH2:24][CH3:25])=[O:22])#N>CN(C)C=O>[Cl:3][C:4]1[CH:17]=[CH:16][C:7]2[N:8]([CH3:15])[C:9](=[O:14])[CH:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[S:11](=[O:13])(=[O:12])[C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 69336Ethyl cyanoformateHCID 5360545SodiumHCID 20492773HCID 20492773, compound

Product 1

HCID 20492743HCID 20492743, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (5.13 g, 60% oil dispersion, washed with dry petroleum ether) in dimethylformamide (110 ml) was added 7-chloro-4-methyl-2H-1,4-benzothiazin-3(4H)one 1,1-dioxide (30 g) at 5° to 10° C. The mixture was allowed to warm to room temperature and stirred for 15 minutes for the preparation of the sodium salt. The reaction mixture was then cooled in an ice bath and a solution of ethyl cyanoformate (16.29 g) in dimethylformamide (15 ml) was added dropwise over 30 minutes. After being stirred for one hour, the mixture was quenched with acetic acid (14 ml), poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and evaporated under reduced pressure. The oily residue was crystallized from ethanol to afford 31 g of 7-chloro-2-ethoxycarbonyl-4-methyl-2H-1,4-benzothiazin-3(4H)one 1,1-dioxide, mp 86° to 91° C. (melt).

Workup

  1. temperatureThe reaction mixture was then cooled in an ice bath
  2. customthe mixture was quenched with acetic acid (14 ml)
  3. additionpoured into ice water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe oily residue was crystallized from ethanol

Sources & evidence

ORD record
ord-a4fce4e58d3146cc852cefe4abd506f6
Source dataset
uspto-grants-1983_08
Patent number
US04397849

Reaction notes

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