Sodium → 2-(1-phenyl-1H-tetrazol-5-yl-thiomethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 2396767Notes

Reaction equation

HRID 2396767 reaction equation
[Na].[SH:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[N:5][N:4]=1.Cl[CH2:15][N:16]1[C:20](=[O:21])[CH:19]([CH2:22][CH2:23][CH3:24])[NH:18][S:17]1(=[O:26])=[O:25]>CN(C=O)C>[C:8]1([N:7]2[C:3]([S:2][CH2:15][N:16]3[C:20](=[O:21])[CH:19]([CH2:22][CH2:23][CH3:24])[NH:18][S:17]3(=[O:25])=[O:26])=[N:4][N:5]=[N:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 194244252-Chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 153405132-(1-phenyl-1H-tetrazol-5-yl-thiomethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sodium salt of 5-mercapto-l-phenyl-1H-tetrazole (0.42 g) ##STR16## was added to a solution of 2-chloromethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1, 1-dioxide (0.44 g) in DMF (10 ml), and the resulting mixture was allowed to react at 50° C. for 6 hours and then cooled. The mixture was poured into ice/water, extracted with ethyl acetate, and the organic layer was washed with water and brine, dried, and concentrated in vacuo. The residue was purified by flash chromatography (35% ethyl acetate in hexane) to afford 0.69 g (96%) of 2-(1-phenyl-1H-tetrazol-5-yl-thiomethyl)-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: R1 =H; R2 =propyl;

Workup

  1. customto react at 50° C. for 6 hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with water and brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-754f5aa383f64f249e995399642a71a2
Source dataset
uspto-grants-1996_02
Patent number
US05494925

Reaction notes

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