Sodium → HCID 18986166, compound

HRID 2396785Notes

Reaction equation

HRID 2396785 reaction equation
Cl[CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][CH3:11])[N:5]([CH2:12][CH3:13])[S:4]1(=[O:15])=[O:14].[Na].[SH:17][C:18]1[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:21]=[N:20][N:19]=1>CN(C=O)C>[C:23]1([N:22]2[C:18]([S:17][CH2:2][N:3]3[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][CH3:11])[N:5]([CH2:12][CH3:13])[S:4]3(=[O:15])=[O:14])=[N:19][N:20]=[N:21]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 19424415HCID 19424415, compoundHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 18986166HCID 18986166, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloromethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.5 g; 1.96 mmol) and sodium salt of 5-mercapto-1-phenyl-1H-tetrazole (0.39 g; 1.98 mmol) (Formula III: M+ =Na+ ; X=S; R4 = ##STR24## in 10 ml of DMF was allowed to react at 80° C for 11 hours and then cooled. The mixture was poured into ice/water containing saturated sodium bicarbonate solution, extracted with ether/ethyl acetate (1:1; 250 ml), and the organic layer was washed with water and brine, dried, and concentrated in vacuo. The residue was purified by silica gel chromatography (35% ethyl acetate in hexane) to afford 0.56 g (72%) of 2-(1-phenyl-1H-tetrazol-5-yl-thiomethyl)-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: ##STR25## as an oil.

Workup

  1. customto react at 80° C for 11 hours
  2. temperaturecooled
  3. extractionextracted with ether/ethyl acetate (1:1; 250 ml)
  4. washthe organic layer was washed with water and brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4477ddd607ba401db181c3600eb0c68e
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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